- Corrected order in the simultaneous debenzylation-acetolysis of methyl 2,3,4,6-tetra-O-benzyl-α-d-glucopyranoside
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The benzyl groups of methyl 2,3,4,6-tetra-O-benzyl-α-d-glucopyranoside were cleaved in the order of 6-O-Bn > 3-O-Bn > 4-O-Bn > 2-O-Bn under acid-mediated conditions in acetic anhydride. The order is a correction of that previously reported.
- Cao, Yang,Yamada, Hidetoshi
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p. 909 - 911
(2007/10/03)
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- A facile regioselective 1,6-O-diacetylation method of methyl- glycopyranosides and their dimethyl phosphonates
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A general method of 1,6-di-O-acetylation of methyl-α/β- glycopyranosides and a strategy to synthesize protected dimethyl (2,3,4-tri- O-benzyl-α-D-glycosyl) phosphonate having a free OH at C-6 are reported.
- Zhang, Guang-Tao,Guo, Zhong-Wu,Hui, Yong-Zheng
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p. 1907 - 1917
(2007/10/03)
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- Synthesis of a pentasaccharide and a heptasaccharide corresponding to an ovarian glycoprotein; studies towards glycosylations
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The syntheses of pentasaccharide I and heptasaccharide II, which correspond to an ovarian O-glycoprotein, are presented. The protected pentasaccharide 1 was prepared by condensing a trisaccharide donor (18c) with a disaccharide acceptor (8b), while conden
- Spijker,Westerduin,Van Boeckel
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p. 6297 - 6316
(2007/10/02)
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- α-Glucosidase Inhibitors, 6. - Synthesis of 1,6-Anhydro-D-glucose and -D-galactose Derivatives - Preparation of 1-Deoxynojirimycin
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Methyl 2,3-di-O-benzyl-D-glucopyranoside (2) is transformed in the presence of p-toluenesulfonic acid and 2,2,2-trichloro- or 2,2,2-trifluoroethanol into the 4-O-unprotected 1,6-anhydropyranose 4.The amount of 1,6-anhydrofuranose 5, formed as a byproduct of this reaction, can be increased by longer reaction times.Similarly, from methyl 2,3-di-O-benzyl-D-galactopyranoside (9) the corresponding 1,6-anhydro compounds 10 and 12 were obtained. 1-Deoxynojirimycin (31) is obtained from the 5-O-unprotected 1,6-anhydroglucofuranose 5 in a few steps.The stereoselectiveintroduction of nitrogen at C-5 is reached by inversion of the configuration of the 5-OH group through oxidation and reduction and subsequent triflate activation for the invertive azide group introduction
- Schmidt, Richard R.,Michel, Josef,Ruecker, Ernst
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p. 423 - 428
(2007/10/02)
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- Building Units of Oligosaccharides, XLVII. - Synthesis of Tri- and Tetrasaccharide Sequences of N-Glycoproteins Including a β-D-Mannosidic Linkage
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The trisaccharides α-D-Man-p-(1 -> 6)-β-D-Man-p-(1 -> 4)-D-GlcNAc (37) and α-D-Man-p-(1 -> 3)-β-D-Man-p-(1 -> 4)-D-GlcNAc (43) as well as the key tetrasaccharide α-D-Man-p-(1 -> 3)- 6)>-β-D-Man-p-(1 -> 4)-D-GlcNAc (51), which are parts of th
- Paulsen, Hans,Lebuhn, Rolf
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p. 1047 - 1072
(2007/10/02)
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