Tetrahedron

Synthesis of the first pseudosugar-C-disaccharide. A potential antigen for eliciting glycoside-bond forming antibodies with catalytic groups

C Barbaud, M Bols, I Lundt, MR Sierks

文献索引：Barbaud; Barbaud, Christel; Bols; Bols, Mikael; Lundt; Lundt, Inge; Sierks; Sierks, Michael R. Tetrahedron, 1995 , vol. 51, # 33 p. 9063 - 9078

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被引用次数: 20

摘要

A number of synthetic routes to the first pseudo-C-disaccharide ever prepared has been studied. The compound, methyl 7-((1S, 3R, 4R, 5S, 6S)-1-amino-3-hydroxymethyl-4, 5, 6trihydroxycyclohexyl)-6, 7-dideoxy-α-D-gluco-heptopyranoside (1), is structurally related to cellobiose, but includes a crucial amino-functionality at the pseudoanomeric centre. It was prepared by 1, 2-addition of the anion of methyl 6, 7-dideoxy-2, 3, 4-tri-O-benzyl-α-D-gluco ...