Affordable Access

Publisher Website

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

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
51
Issue
33
Identifiers
DOI: 10.1016/0040-4020(95)00505-3

Abstract

Abstract 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-hept-6ynopyranoside to ( 4R, 5S, 6R)-3-benzyloxymethyl-4,5,6-tribenzyloxy-2-cyclohexenone followed by stereoselective conversion of the tertiary alcohol to azide and finally reduction.

There are no comments yet on this publication. Be the first to share your thoughts.