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Title Carbohydrate chemistry : proven synthetic methods / edited by Pavol Kovác
Publish Info Boca Raton, FL : CRC Press, ©2012-<c2015>
Imprint ©2012

Bookmark this record as <https://olc1.ohiolink.edu:443/record=b30147575>

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Miami U King Library (2nd floor) QD322.S95 C37 2012 v.4 AVAILABLE
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Contents

 Foreword / Derek Hortonxiii
 Foreword / Paul Kosmaxv
 Foreword / Bert Fraser-Reidxvii
 Introductionxix
 Contributorsxxiii
pt. I Synthetic Methods 
1.Acetolysis of 6-Deoxysugars Controlled by Armed---Disarmed Effect / Michalangelo Parrilli3
 Experimental Methods4
 General Methods4
 Acetolysis Procedure6
 Acknowledgments7
 References10
2.NaH/Im2SO2-Mediated Preparation of Hex-2- and Hex-3-Enopyranoside Enol Ethers / Marie-Christine Scherrmann11
 Experimental Methods16
 General Methods16
 Methyl 2,6-Di-O-Benzyl-4-Deoxy-3-O-Naphthylmethyl-β-D-threo-Hex-3-Enopyranoside(13)16
 Methyl 2-O-Benzyl-4-Deoxy-3-O-p-Methoxybenzyl-6-O-Methoxymethyl-β-D-threo-Hex-3-Enopyranoside (15)17
 3-Azidopropyl 2-Acetamido-3,6-Di-O-Benzyl-2,4-Dideoxy-β-D-threo-Hex-3-Enopyranosyl-(1 [→] 4)-2,3,6,-Tri-O-Benzyl-β-D-Glucopyranosyl-(1 [→] 2)-3,4-Di-O-Benzyl-α-L-Rhamnopyranoside (17)17
 Methyl 3,4,6-Tri-O-Benzyl-2-Deoxy-β-D-threo-Hex-2-Enopyranoside (19)18
 2-Deoxy-3,4-O-Isopropylidene-6-O-Trityl-β-D-threo-Hex-2-Enopyranosyl-(1 [→] 4)-2,3:5,6-Di-O-Isopropylidene-Aldehydo-D-Glucose Dimethyl Acetal (21) 
 Methyl 3,4-Di-O-Benzyl-2,6-Dideoxy-α-L-threo-Hex-2-Enopyranoside (23)19
 References26
3.Enhancement of the Rate of Purdie Methylation by Me2S Catalysis / Pavol Kovac27
 Experimental Methods29
 General Methods29
 General Procedure29
 Methylation of Methyl 3-O-Benzyl-β-D-Galactopyranoside (1)30
 Methylation of Methyl 6-O-Trityl-β-D-Galactopyranoside (3)31
 Methylation of Methyl 6-O-Trityl-α-D-Glucopyranoside (5)32
 Methylation of Methyl 2,3-Di-O-Benzyl-6-O-Benzoyl-β-D-Glucopyranoside (7)33
 Acknowledgment35
 References42
4.Synthesis of Oligosaccharides by Preactivation-Based Chemoselective Glycosylation of Thioglycosyl Donors / Xuefei Huangs43
 Experimental Methods45
 General Methods45
 P-Toluenesulfenyl Chloride (1)2546
 P-Tolyl 6-O-(2,3,4-Tri-O-Benzoyl-6-O-Tert-Butyldiphenylsilyl-β-D-Glucopyranosyl)-2,3,4-Tri-O-Benzyl-1-Thio-β-D-Glucopyranoside (4)46
 Methyl-2-O-Benzoyl-3-O-Benzyl-4-O-tert-Butyldimethylsilyl)-6-0-p-Methoxybenzyl-β-D-Glucopyranosyl-(1 [→] 3)-4,6-O-Benzylidene-2-Deoxy-2-N-Phthalimido-β-D-Galactopyranosyl-(1 [→] 4)-2,3-Di-O-Benzyl-6-O-p-Methoxybenzyl-β-D-Glucopyranoside (8)47
 Acknowledgment48
 References50
5.The Use of Hypophosphorous Acid in Radical Chain Deoxygenation of Carbohydrates / Alice Voss53
 Experimental Methods56
 General Method56
 Methyl 2,3-O-Isopropylidene-4-O-[(Methylsulfanyl)thiocarbonyl]-6-O-Triphenylmethyl-α-D-Mannopyranoside (2)57
 Methyl 4-Deoxy-2,3-O-Isopropylidene-6-O-Triphenylmethyl-α-D-Lyxo-Hexopyranoside (3)57
 1,2:5,6-Di-O-Isopropylidene-3-O-[(Methylsulfanyl)thiocarbonyl]-α-D-Glucofuranose (5)58
 3-Deoxy-1,2:5,6-Di-O-Isopropylidene-α-D-Ribo-Hexofuranose (6)58
 1,2:4,5-Di-O-Isopropylidene-3-O-[(Methylsulfanyl)thiocarbonyl]-β-D-Fructopyranose (8)58
 3-Deoxy-1,2:4,5-Di-0-Isopropylidene-β-D-Erythro-Hex-2-Ulopyranose (9)59
 1,6-Anhydro 4-O-Benzyl-2-Deoxy-2-C-Methyl-3-O-[(Methylsulfanyl)thiocarbonyl]-β-D-Glucopyranose (11)59
 1,6-Anhydro 4-O-Benzyl-2,3-Dideoxy-2-C-Methyl-β-D-Ribo-Hexopyranose (12)59
 References63
6.Diphenylsulfoxide-Trifluoromethanesulfonic Anhydride: A Potent Activator for Thioglycosides / Gijsbert A. van der Marel67
 Experimental Methods68
 General Methods68
 Methyl (4-O-Acetyl-2,3-Di-O-β-D-Mannopyranosyl)-(1 [→] 6)-(Methyl 2,3,4-Tri-O-Benzyl-α-D-Glucopyranosid)uronate (6)69
 Acknowledgments70
 References71
7.Preparation of Glycosyl Chlorides from Glycopyranoses/Glycopyranoses under Mild Conditions / Kwok-Kong T. Mong73
 Introduction73
 General TCT/DMF Chlorination Protocols75
 Experimental Methods75
 General Methods75
 TCT/DMF Chlorination Protocol A for Preparation of Glycosyl Chlorides 1a and 2a76
 TCT/DMF Chlorination Protocol B for Preparation of Glycosyl Chlorides 3a and 4a76
 2,3,4,6-Tetra-O-Acetyl-α-D-Glucopyranosyl Chloride (1a)76
 2,3,4,6-Tetra-O-Acetyl-α-D-Mannopyranosyl Chloride (2a)77
 2,3,4,6-Tetra-O-Benzyl-α-D-Galactopyranosyl Chloride (3a)77
 2,3:5,6-Di-O-Isopropylidene-α-D-Mannofuranosyl Chloride (4a)77
 Acknowledgment78
 References81
8.C-Glycosylation Starting from Unprotected O-Glycosides / Francesco Nicotra83
 Experimental Methods84
 General Methods84
 3-(α-D-Galactopyranosyl)prop-l-Ene (2)85
 Bicyclic Iodoethers (3)85
 Methyl (2R)-2-Acetamido-3-(α-D-Galactopyranosylpropylthio) propanoate (4)85
 Acknowledgments86
 References89
9.Palladium-Catalyzed Sonogashira Coupling on p-lodophenyl α-D-Mannopyranoside / Mohamed Touaibia91
 Experimental Methods92
 General Methods92
 3-[4-(2,3,4,6-Tetra-O-Acetyl-α-D-Mannopyranosyloxy)phenyl]prop-2-Yn-l-ol (2)92
 Acknowledgments93
 References94
10.Synthesis by "Click Chemistry" of an α-D-Mannopyranoside Having a 1,4-Disubstituted Triazole as Aglycone / Mohamed Touaibia95
 Experimental Methods96
 General Methods96
 Methyl2-{[4-(2,3,4,6-Tetra-O-Acetyl-α-D-Mannopyranosyloxy)methyl]-1H-l,2,3-Triazol-l-yl]}Acetate (2)96
 Acknowledgments97
 References98
11.Synthesis of Methyl Glycuronates by Chemo-and Regioselective TEMPO/BAIB-Oxidation / Jeroen D.C. Codee99
 Experimental Methods101
 General Methods101
 Phenyl3-O-Benzoyl-2-Deoxy-2-Phthalimido-1-Thio-β-D- Glucopyranosyluronic Acid (2)102
 Methyl(Phenyl3-O-Benzoyl-2-Deoxy-2-Phthalimido-1-Thio-β-D-Glucopyranoside) Uronate (3)102
 Acknowledgments103
 References104
12.Synthesis of Sugar Nucleotides: A Phosphoramidite Approach / Gijsbert A. van der Marel107
 Experimental Methods109
 General Methods109
 Uridine5'-(2-Acetamido-2-Deoxy-α-D-GlucopyranosylDiphosphate)Disodium Salt(5)109
 References112
13.Conversion of N-2,2,2-Trichloroethoxycarbonyl-Protected 2-Aminoglycosides into N-Alkylated 2,3-N, O-Carbonyl Glycosides / Thomas Ziegler113
 Experimental Methods115
 General Methods115
 General Procedure115
 2-Trimethylsilylethyl 4,6-O-Benzylidene-2-Deoxy-2-(2,2,2-Trichlorethoxycarbamido)-β-D-Glucopyranoside (1)115
 2-Trimethylsilylethyl 2-Amino-2-N-Benzyl-4,6-O-Benzylidene-2,3-N, O-Carbonyl-2-Deoxy-β-D-Glucopyranoside (2)116
 Phenyl 4,6-O-Benzylidene-2-Deoxy-1-Thio-2-(2,2,2-Trichlorethoxycarbamido)-β-D-Glucopyranoside (3)116
 Phenyl 2-Amino-2-N-Benzyl-4,6-O-Benzylidene-2,3-N, O-Carbonyl-2- Deoxy-1-Thio-β-D-Glucopyranoside (4)117
 Phenyl 2-Amino-4,6-O-Benzylidene-2,3-N, o-Carbonyl-2-Deoxy-2-N-(4-Nitrobenzyl)-1-Thio-β-D-Glucopyranoside (5)117
 Phenyl 2-Amino-4,6-O-Benzylidene-2,3-N, o-Carbonyl-2-Deoxy-2-N-(4-Methoxybenzyl)-1-Thio-β-D-Glucopyranoside (6)117
 Phenyl 2-Amino-4,6-O-Benzylidene-2,3-N, o-Carbonyl-2-Deoxy-2-N-(Prop-2-Enyl)-1-Thio-β-D-Glucopyranoside (7)118
 Phenyl 2-Amino-4,6-O-Benzylidene-2,3-N, o-Carbonyl-2-Deoxy-2-N-(Prop-2-Ynyl)-1-Thio-β-D-Glucopyranoside (8)118
 Phenyl 4,6-O-Benzylidene-2-Deoxy-1-Thio-2-(2,2,2-Trichlorethoxycarbamido)-β-D-Galactopyranoside (9)118
 Phenyl 2-Amino-2-N-Benzyl-4,6-O-Benzylidene-2,3-N, o-Carbonyl-2-Deoxy-l-Thio-β-D-Galactopyranoside (10)119
 References127
14.TIBAL-lnduced Rearrangement: Synthesis of gem-Difluorocarbagalactose / Yves Bleriot129
 Experimental Methods131
 General Methods131
 Rearrangement of 1 into 2,3,4-Tri-O-Benzyl-6,7,8-Trideoxy-5a-Difluoro-5a-Carba-α-D-Galacto-Oct-6-Ynopyranose (4) and 2,3,4-Tri-O-Benzyl-6,7,8-Trideoxy-5a-Difluoro-5a-Carba-β-D-Galacto-Oct-6-Ynopyranose (5)132
 Acknowledgment132
 References135
15.Pyranose-Fused Butenolides: An Expedient Preparation from Furanose Synthons / Amelia Pilar Rauter137
 Experimental Methods140
 General Methods140
 1,2:5,6-Di-O-Isopropylidene-α-D-Ribo-Hexofuranosid-3-Ulose (1)141
 3-Deoxy-3-C-[(Z)-(Ethoxycarbonyl)methylene]-1,2:5,6-Di-O-Isopropylidene-α-D-Ribo-Hexofuranose (2) and 3-Deoxy-3-C-[(E)-(Ethoxycarbonyl)methylene]-1,2:5,6-Di-O-Isopropylidene-α-D-Ribo-Hexofuranose (3)141
 3-C-(Carboxymethylene)-3-Deoxy-D-Ribo-Hexopyranose-3', 2-Lactone (4)141
 3-Deoxy-3-C-[(Z)-(Ethoxycarbonyl)methylene]-1,2-O-Isopropylidene-α-D-Ribo-Hexofuranose (5)142
 3-Deoxy-3-C-[(Z)-(Ethoxycarbonyl)methylene]-1,2-O-Isopropylidene-6-O-Pivaloyl-α-D-Ribo-Hexofuranose (6) and 3-Deoxy-3-C-[(Z)-(Ethoxycarbonyl)methylene]-1,2-O-Isopropylidene-5,6-Di-O-Pivaloyl-α-D-Ribo-Hexofuranose (7)142
 3-C-(Carboxymethylene)-3-Deoxy-6-O-Pivaloyl-D-Ribo-Hexopyranose-3',2-Lactone (8)143
 1,4,6-Tri-O-Acetyl-3-C-(Carboxymethylene)-3-Deoxy-D-Ribo-Hexopyranose-3',2-Lactone (9)143
 5-O-Tert-Butyldimethylsilyl-1,2-O-Isopopylidene-α-D-Erythro-Pentofuranos-3-Ulose (10)144
 5-0-Tert-Butyldimethylsily1-3-Deoxy-3-C-[(Z)-(Ethoxycarbonyl)methylene]-1,2-O-Isopropylidene-α-D-Erythro-Pentofuranose (11) and 5-O-Tert-Butyldimethylsilyl-3-Deoxy-3-C-[(E)-(Ethoxycarbonyl)methylene]-1,2-O-Isopropylidene-α-D-Erythro-Pentofuranose (12)144
 3-C-(Carboxymethylene)-3-Deoxy-D-Erythro-Pentopyranose-3',2-Lactone (13)145
 Acknowledgment145
 References157
16.Glycal Dimerization with High Diastereoselectivity / Katja Michael159
 Experimental Methods160
 General Methods160
 General Method for the Dimerization of Glycals161
 1,3,4,6-Tetra-O-Acetyl-2-C-(4,6-Di-O-Acetyl-2,3-Dideoxy-α-D-Erythro-Hex-2-Enopyranosyl)-2-Deoxy-α/β-D-Glucopyranose (2a, 2b)162
 Acknowledgments164
 References166
17.Regioselective Debenzylation of C-Glycosylpropene / Francesco Nicotra167
 Experimental Methods168
 General Methods168
 General Procedure for Iodocyclization169
 β-Elimination169
 3-C-(3,4,6-Tri-O-Benzyl-α-D-Glucopyranosyl)Prop-1-Ene (3)169
 3-C-(3,4,6-Tri-O-Benzyl-α-D-Fructofuranosyl)Prop-1-Ene (6)170
 Acknowledgment171
 References173
18.Synthesis of Azido-Functionalized Carbohydrates for the Design of Glycoconjugates / Sebastien Vidal175
 Experimental Methods176
 General Methods176
 General Procedure for Glycosylation177
 1-Azido-3,6-Dioxaoct-8-yl 2,3,4,6-Tetra-O-Acetyl-β-D-Galactopyranoside 2177
 1-Azido-3,6-Dioxaoct-8-yl 2,3,6,2',3',4',6'-Hepta-O-Acetyl-β-Lactoside 4178
 Acknowledgments178
 References180
19.Synthesis of Thioglycosides and Thioimidates from Glycosyl Halides / Alexei V. Demchenko181
 Experimental Methods182
 1,3-Benzoxazol-2-yl 2,3,4,6-Tetra-O-Acetyl-l-Thio-β-D-Glucopyranoside (3)182
 Methyl (Phenyl 5-Acetamido-4,7,8,9-Tetra-O-Acetyl-3,5-Dideoxy-2-Thio-D-Glycero-α-D-Galato-Non-2-Ulopyranosid)onate (6)183
 Acknowledgments183
 References185
20.Synthesis of Thioglycosides and Thioimidates from Peracetates / Alexei V. Demchenko187
 Experimental Methods189
 General Methods189
 Phenyl 2,3.4,6-Tetra-O-Acetyl-1-Thio-β-D-Glucopyranoside (2)189
 4,5-Dihydro-1,3-Thiazol-2-yl 2,3,4,6-Tetra-O-Acetyl-1-Thio-β-D-Glucopyranoside (3)190
 Ethyl 2,3,4,6-Tetra-O-Acetyl-1-Thio-β-D-Glucopyranoside (4)190
 P-Tolyl 2,3.4.6-Telra-O-Acetyl-1-Thio-β-D-Glucopyranoside (5)191
 Acknowledgment191
 References195
pt. II Synthetic Intermediates 
21.2-Acetamido-4,6-O-BenzyIidene-2-Deoxy-D-GIucopyranose / Sebastien Vidal199
 Experimental Methods200
 General Methods200
 2-Acetamido-4,6-O-Benzylidene-2-Deoxy-D-Glucopyranose (2)200
 Acknowledgment202
 References203
22.Synthesis of 1,3,4,6-Tetra-O-Acetyl-2-Azido-2-Deoxy-α,β-D-Glucopyranose and 2-Azido-4,6-O-Benzylidene-2-Deoxy-α,β-D-Glucopyranose / Manuel Martin-Lomas205
 Experimental Methods206
 General Methods206
 Preparation of Trifluoromethanesulfonyl Azide (TfN3) Solution207
 1,3,4,6-Tetra-O-Acetyl-2-Azido-2-Deoxy-α,β-D-Glucopyranose (2)207
 2-Azido-4,6-O-Benzylidene-2-Deoxy-α,β-D-Glucopyranose (3)208
 References211
23.An Easy Access to 2,3,4,6-Tetra-O-Benzyl-D-Galactopyranose and 2,3,6-Tri-O-Benzyl-D-Glucopyranose / Lorenzo Guazzelli213
 Experimental Methods214
 General Methods214
 Benzyl 2,3,4,6-Tetra-O-Benzyl-β-D-Galactopyranosyl-(1 [→] 4)-2,3,6-Tri-O-Benzyl-β-D-Glucopyranoside (II)215
 2,3,4,6-Tetra-O-Benzyl-D-Galactopyranose (IV), 2,3,6-Tri-O-Benzyl-D-Glucopyranose (V) and 1-O-Acetyl-2,3,4,6-Tetra-O-Benzyl-β-D-Galactopyranose (III)216
 References220
24.Benzyl 2,3,6,2',3',6'-Hexa-O-Benzyl-β-Cellobioside / Pavol Kovaac221
 Experimental Methods222
 General Methods222
 Benzyl 2,3,6,2',3'-Penta-O-Benzyl-4',6'-O-Benzylidene-α-Cellobioside (2A) and Benzyl 2,3,6,2',3'-Penta-O-Benzyl-4',6'-O-Benzylidene-β-Cellobioside (2B)223
 Benzyl 2,3,6,2',3',6'-Hexa-O-Benzyl-β-Cellobioside (3) and Benzyl 2,3,6,2',3',4'-Hexa-O-Benzyl-β-Cellobioside (9)224
 Acknowledgment225
 References230
25.One-Step Syntheses of 1,2,3,5,6-Penta-O-Benzoyl-α,β-D-Galactofuranose and 1,2,3,5-Tetra-O-Benzoyl-α,β-D-Arabinofuranose / Rosa M. de Lederkremer231
 Experimental Methods233
 General Methods233
 1,2,3,5,6-Penta-O-Benzoyl-α,β-D-Galactofuranose (1α and 1β)233
 1,2,3,5-Tetra-O-Benzoyl-α,β-D-Arabinofuranose (2αβ), 1,2,3,5-Tetra-O-Benzoyl-α-D-Arabinofuranose (2α) and 1,2,3,4-Tetra-O-Benzoyl-α-D-Arabinopyranose (3)234
 Acknowledgments235
 References237
26.Stereoselective Synthesis of α-C-Sialyl Compounds / Robert J. Linhardt239
 Introduction239
 Experimental Methods240
 General Methods240
 SmI2 Mediated C-Sialylation: 4,4-Dimethyl-l-[Methyl (5-Acetamido-4,7,8,9-Tetra-O-Acetyl-3,5-Dideoxy-D-Glycera-α-D-Galacto-Non-2-Ulopyranosyl)onate]cyclohexanol (3)240
 References242
27.Synthesis of O-Acetylated N-Acetylneuraminic Acid Glycal / Leonid O. Kononov245
 Experimental Methods246
 General Methods246
 Methyl (5-Acetamido-4,7,8,9-Tetra-O-Acetyl-3,5-Dideoxy-β-D-Glycero-D-Galacto-Non-2-Ulopyranosyl)onate Chloride (2)246
 Methyl (5-Acetamido-4,7,8,9-Tetra-O-Acetyl-3,5-Dideoxy-2,6-Anhydro-D-Glycero-D-Galacto-Non-2-Enopyranos)onate (3)249
 Acknowledgment250
 References250
28.Substituted Benzyl Glycosides of N-Acetylneuraminic Acid / N.V. Bovin251
 Experimental Methods253
 General Methods253
 Methyl {4-[(Tert-Butyloxycarbonyl)glycylarmido]benzyl 5-Acetamido-4,7,8,9-Tetra-O-Acetyl-3,5-Dideoxy-D-Glycero-D-Galacto-Non-2-Ulopyranosid}onate (3)253
 4-[(Tert-Butyloxycarbonyl)glycylamido]benzyl 5-Acetamido-3,5-Dideoxy-D-Glycero-D-Galacto-Non-2-Ulopyranosidonic Acid (5)256
 4-(Glycylamido)benzyl 5-Acetamido-3,5-Dideoxy-D-Glycero-D-Galacto-Non-2-Ulopyranosidonic Acid (6)256
 4-[(4-Nitrophenoxy)adipoylglycylamido]benzyl 5-Acetamido-3,5-Dideoxy-D-Glycero-D-Galacto-Non-2-Ulopyranosidonic Acid (8)257
 Acknowledgment257
 References257
29.Synthesis of 1,5-Di-C-Alkyl 1,5-Iminoxylitols Related to 1-Deoxynojirimycin / Jean-Bernard Behr259
 Introduction259
 Experimental Methods261
 General Methods261
 1,5-Di-(1/2-Benzotriazolyl)-N-Benzyl-1,5-Dideoxy-1,5-Iminoxylitol (4)261
 2,3,4-Tri-O-Acetyl-1,5-Di-C-Allyl-N-Benzyl-1,5-Dideoxy-1,5-Iminoxylitol (5)262
 Meso-(1R,5S)-, Meso-(1S,5R), and Rac-(1R,5R)-2,3,4-Tri-O-Acetyl-1,5-Di-C-Allyl-1,5-Dideoxy-1,5-Iminoxylitol (6a, 6b, and 6c)262
 Acknowledgment263
 References267
30.Synthesis of 1,6-Anhydro 2,3,5-Tri-O-Benzoyl-α-D-Galactofuranose / Nirmolendu Roy269
 Experimental Methods270
 General Methods270
 6-O-Benzyl-1,2:3,4-Di-O-Isopropylidene-α-D-Galactopyranose (2)270
 Methyl 2,3,5-Tri-O-Benzoyl-6-O-Benzyl-β-D-Galactofuranoside (4)270
 1,6-Anhydro-2,3,5-Tri-O-Benzoyl-α-D-Galactofuranose (5)271
 1,6-Anhydro-α-D-Galactofuranose (6)271
 1,6-Anhydro-2,3,5-Tri-O-Acetyl-α-D-Galactofuranose (7)271
 Acknowledgment271
 References274
31.Synthesis of Prop-2-Ynyl 2,3,4,6-Tetra-O-Acetyl-α-D-Mannopyranoside / Rene Roy275
 Experimental Methods276
 General Methods276
 Prop-2-Ynyl 2,3,4,6-Tetra-O-Acetyl-α-D-Mannopyranoside (2)276
 Acknowledgments277
 References278
32.Synthesis of 3-C-(2,3,4,6-Tetra-O-Acetyl-β-D-Galactopyranosyl) prop-1-Ene / Rene Roy279
 Experimental Methods280
 General Methods280
 2,3,4,6-Tetra-O-Acetyl-α-D-Galactopyranosyl Bromide (1)280
 3-C-(2,3.4,6-Tetra-O-Acetyl-β-D-Galactopyranosyl)Prop-l-Ene (2)281
 Acknowledgments281
 References282
33.Synthesis of (E)-Methyl 4-(2,3,4,6-Tetra-O-Acetyl-β-D-Galactopyranosyl) but-2-Enoate by Cross-Metathesis Reaction / Rene Roy285
 Experimental Methods286
 General Methods286
 (E)-Methyl 4-(2,3,4,6-Tetra-O-Acetyl-β-D-Galactopyranosyl)but-2- Enoate (2)286
 Acknowledgment287
 References288
34.Preparation of O-β-D-Galactopyranosyl-hydroxylamine / Rene Roy289
 Experimental Methods290
 General Methods290
 O-(2,3,4,6-Tetra-O-Acetyl-β-D-Galactopyranosyl)-N-Hydroxysuccinimide (2)290
 O-β-D-Galactopyranosylhydroxylamine (3)291
 Acknowledgments291
 References293
35.Synthesis of 2,3,4,6-Tetra-O-Acetyl-1,5-Anhydro-D-Lyxo-Hex-1-Enitol and Its Conversion into a Hex-3-Enopyranosid-2-Ulose Analogue of Levoglucosenone / Oscar Varela295
 Experimental Methods296
 General Methods296
 2,3,4,6-Tetra-O-Acetyl-1,5-Anhydro-D-Lyxo-Hex-1-Enitol (3)297
 Benzyl 3,4-Dideoxy-α-D-Glycero-Hex-3-Enopyranosid-2-Ulose (4)298
 Acknowledgments298
 References301
36.Efficient Synthesis of Methyl(Allyl 4-O-Acyl-2,3-Di-O-Benzyl-β-D-Galactopyranosid) uronates from D-Galacturonic Acid / Christian Vogel303
 Experimental Methods306
 General Methods306
 1,2,3,4-Tetra-O-Acetyl-α-D-Galactopyranuronic Acid (11)307
 Methyl 1,2,3,4-Tetra-O-Acetyl-α-D-Galactopyranuronate (12)308
 Methyl 2,3,4-Tri-O-Acetyl-α-D-Galactopyranosyluronate Bromide (13)308
 Methyl (Allyl 2,3,4-Tri-O-Acetyl-β-D-Galactopyranosid)uronate (14)308
 Methyl (Allyl β-D-Galactopyranosid)uronate (19)309
 Regioselective Ring Opening in Orthoester Structures 20 and 21309
 Methyl (Allyl 4-O-Acetyl-β-D-Galactopyranosid)uronate (22)309
 Methyl (Allyl 4-O-Benzoyl-β-D-Galactopyranosid)uronate (23)310
 Benzylation of Compounds 22 and 23310
 Methyl (Allyl 4-O-Acetyl-2,3-Di-O-Benzyl-β-D-Galactopyranosid)uronate (1)310
 Methyl (Allyl 4-O-Benzoyl-2,3-Di-O-Benzyl-β-D-Galactopyranosid)uronate (2)310
 Methyl (Allyl 2,3-Di-O-Benzyl-β-D-Galactopyranosid)uronate (5)311
 References326
37.Methyl(Ethyl 2,3,5-Tri-O-Benzoyl-1-Thio-α,β-D-Galactofuranosid)uronate / Nirmolendu Roy327
 Experimental Methods329
 General Methods329
 Tert-Butyl 1,2:3,4-Di-O-Isopropylidene-α-D-Galactopyranuronate (2)330
 Methyl (Methyl α,β-D-Galactofuranosid)uronate (3)330
 Methyl (Methyl α-D-Galactofuranosid)uronate (3α)330
 Methyl (Methyl β-D-Galactofuranosid)uronate (3β)330
 Methyl (Methyl 2,3,5-Tri-O-Benzoyl-α,β-D-Galactofuranosid)uronate (4)330
 Methyl (Methyl 2,3,5-Tri-O-Benzoyl-α-D-Galactofuranosid)uronate (4α)331
 Methyl (Methyl 2,3,5-Tri-O-Benzoyl-β-D-Galactofuranosid)uronate (4β)331
 Methyl 1-O-Acetyl-2,3,5-Tri-O-Benzoyl-α,β-D-Galactofuranuronate (5)331
 Methyl 1-O-Acetyl-2,3,5-Tri-O-Benzoyl-α-D-Galactofuranuronate (5α)331
 Methyl 1-O-Acetyl-2,3,5-Tri-O-Benzoyl-β-D-Galactofuranuronate (5β)332
 Methyl (Ethyl 2,3,5-Tri-O-Benzoyl-1-Thio-α,β-D-Galactofuranosid)uronate (6)332
 Methyl (Ethyl 2,3,5-Tri-O-Benzoyl-1-Thio-α-D-Galactofuranosid)uronate (6α)332
 Methyl (Ethyl 2,3,5-Tri-O-Benzoyl-1-Thio-β-D-Galactofuranosid)uronate (6β)332
 References339
38.P-Tolyl 2,3,5-Tri-O-Benzoyl-1-Thio-α-D-Arabinofuranoside: A Useful Thioglycoside Building Block In The Synthesis Of Oligoarabinofuranosides / Todd L. Lowary341
 Experimental Methods342
 General Methods342
 P-Tolyl 2,3,5-Tri-O-Benzoyl-1-Thio-α-D-Arabinofuranoside343
 Waste Disposal Information344
 Acknowledgments344
 References347
39.Ethylene Dithioacetals of Common Hexoses / Maria Teresa Barros349
 Experimental Methods350
 General Methods350
 General Procedure350
 D-Galactose Ethylene Dithioacetal (1)350
 D-Glucose Ethylene Dithioacetal (2)350
 D-Mannose Ethylene Dithioacetal (3)351
 References354
40.Preparation of 2,6-Anhydro-Aldose Tosylhydrazones / David Goyard355
 Experimental Methods357
 General Methods357
 General Procedure357
 2,6-Anhydro-3,4,5,7-Tetra-O-Benzoyl-D-Glycero-D-Gulo-Heptose Tosylhydrazone (2a)358
 3,4,5,7-Tetra-O-Acetyl-2,6-Anhydro-D-Glycero-D-Gulo-Heptose Tosylhydrazone (2b)358
 3,4,5,7-Tetra-O-Acetyl-2,6-Anhydro-D-Glycera-L-Manno-Heptose Tosylhydrazone (2c)358
 4,5,7-Tri-O-Acetyl-2,6-Anhydro-3-Deoxy-3-Phthalimido-D-Glycero-D-Gulo-Heptose Tosylhydrazone (2d)359
 3,4,5-Tri-O-Acetyl-2,6-Anhydro-D-Manno-Hexose Tosylhydrazone (2e)359
 Acknowledgments359
 References365
41.Preparation of Exo-Glycals from (C-Glycopyranosyl) formaldehyde Tosylhydrazones / David Goyard367
 Experimental Methods369
 General Methods369
 General Procedure369
 2,6-Anhydro-3,4,5,7-Tetra-O-Benzoyl-1-Deoxy-D-Gluco-Hept-1-Enitol (2a)370
 3,4,5,7-Tetra-O-Acetyl-2,6-Anhydro-1-Deoxy-D-Galacto-Hept-1-Enitol (2b)370
 4,5,7-Tri-O-Acetyl-2,6-Anhydro-1,3-Dideoxy-3-Phthalimido-D-Gluco-Hept-1-Enitol (2c)370
 3,4,5-Tri-O-Acetyl-2,6-Anhydro-1-Deoxy-D-Arabino-Hex-1-Enitol (2d)370
 Acknowledgments371
 References375
42.Synthsis of O-(6-Deoxy-α-and β-L-Galactopyranosyl) Hydroxylamines (α-and β-L-Fucopyranosyl-hydroxylamines) / Olivier Renaudet377
 Experimental Methods378
 General Methods378
 O-(2,3,4-Tri-O-Acetyl-6-Deoxy-α-L-Galactopyranosyl)-N-Hydroxyphthalimide (2) and O-(2,3,4-Tri-O-Acetyl-6-Deoxy-β-L-Galactopyranosyl)-N-Hydroxyphthalimide (3)379
 O-(6-Deoxy-α-L-Galactopyranosyl)Hydroxylamine(O-α-L-Fucopyranosylhydroxylamine) (4)380
 O-(6-Deoxy-β-L-Galactopyranosyl)Hydroxylamine(O-β-L-Fucopyranosylhydroxylamine) (5)380
 Acknowledgments381
 References385
43.Functionalization of Terminal Positions of Sucrose---Part I: Synthesis of 2,3,3',4,4'-Penta-O-Benzylsucrose and Differentiation of the Terminal Positions (1,6,6') / S. Jarosz387
 Experimental Methods389
 General Methods389
 1',6,6'-Tri-O-Tritylsucrose (2)390
 2,3,3',4,4'-Penta-O-Benzyl-1',6,6'-Tri-O-TrityIsucrose (3)391
 2,3,3',4,4'-Penta-O-Benzylsucrose (4)391
 2,3,3',4,4'-Penta-O-Benzyl-6,6'-Di-O-p-Nitrobenzoylsucrose (5)392
 2,3,3'4,4'-Penta-O-Benzyl-1'-O-Benzyloxymethyl-6,6'-Di-O-p-Nitrobenzoylsucrose (6)392
 2,3,3',4,4'-Penta-O-Benzyl-1'-O-Benzyloxymethylsucrose (7)392
 2,3,3',4,4'-Penta-O-Benzyl-1'-O-Benzyloxymethyl-6'-O-Tert-Butyldiphenylsilylsucrose (8)393
 Carbohydradte Chemistry: Proven Synthetic Methods 
 1'-O-Benzyloxymethyl-6,6'-Di-O-Tert-Butyldiphenylsilyl-2,3,3'4,4'-Penta-O-Benzylsucrose (9)393
 2,3,3',4,4'-Penta-O-Benzyl-1'-O-Benzyloxymethyl-6-O-Tert-Butyldiphenylsilylsucrose (10)394
 References411
44.Functionalization of Terminal Positions of Sucrose---Part II: Preparation of 1',2,3,3',4,4'-Hexa-O-Benzylsucrose and 6,6'-Bis-O-(2-Hydroxyethyl)-1',2,3,3',4,4'-Hexa-O-Benzylsucrose / S. Jarosz413
 Experimental Methods414
 General Methods414
 6,6'-Di-O-Tritylsucrose (1)416
 1',2,3,3',4,4'-Hexa-O-Acetyl-6,6'-Di-O-Tritylsucrose (1A)417
 1',2,3,3',4,4'-Hexa-O-Benzyl-6,6'-Di-O-Tritylsucrose (2)417
 1',2,3,3',4,4'-Hexa-O-Benzyl-6,6'-Dichloro-6,6'-Dideoxysucrose (3A)418
 6,6'-Di-O-Acetyl-1',2,3,3',4,4'-Hexa-O-Benzylsucrose (4)418
 1',2,3,3',4,4'-Hexa-O-Benzylsucrose (5)419
 6,6'-Di-O-Allyl-1',2,3,3',4,4'-Hexa-O-Benzylsucrose (6)419
 1',2,3,3',4,4'-Hexa-O-Benzyl-6,6'-Bis-(O-Tert-Butoxycarbonylmethylsucrose (7)420
 1',2,3,3',4,4'-Hexa-O-Benzyl-6,6'-Bis-(O-2-Hydroxyethyl) Sucrose (8)420
 References430
 Index431
Description volumes <1-3> : illustrations ; 24 cm
Series Carbohydrate chemistry: proven synthetic methods ; v. 1
Carbohydrate chemistry: proven synthetic methods ; v. 1
Note Vol. 2 edited by: Gijsbert van der Marel, Jeroen Codee; v. 3. edited by René Roy, Sébastien Vidal
Includes bibliographical references and index
Contents Pt. 1. Synthetic methods -- pt. 2. Synthetic intermediates
Subjects Carbohydrates -- Synthesis
Alt Name Kováč, Pavol, 1938- https://id.oclc.org/worldcat/entity/E39PCjHCYrbdv3hPQ37rMThv9C
LC NO QD322.S95 C37 2012
Nal No QD322.S95 C37 2012
Dewey No 547/.27 22
OCLC # 676728385
ISBN 9781439866894 (hardcover ; alk. paper)
1439866899 (hardcover ; alk. paper)
9781439875940 (hardcover ; alk. paper ; v. 2)
1439875944 (hardcover ; alk. paper ; v. 2)
9781466583573 (hardcover ; v. 3)
1466583576 (hardcover ; v. 3)
9781498726917 (hardcover ; v. 4)
1498726917 (hardcover ; v. 4)
9781315120300 (v. 4)
1315120305 (v. 4)
Isn/Std # (OCoLC)676728385 (OCoLC)859196294
LCCN 2011010495 2015004527 2017027677

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