Synthesis of 2-Amino-2-deoxy-D-hexopyranoside-Containing Disaccharides Involving Glycosylation and [3,3] Sigmatropic Rearrangement

Kazuyoshi Takeda, Eisuke Kaji, Hiroko Nakamura, A. AKIYAMA, Yaeko Konda, Yoshihisa Mizuno, Hiroaki Takayanagi, Yoshihiro Harigaya

Synthesis · 1996 · 22 citations · 0 references

Concepts

Abstract

The syntheses of D-mannosamine 15, D-idosamine 16, D-altrosamine 19, and D-tallosamine 20 derivatives of 2-amino-2-deoxy-D-hexopyranoside-containing disaccharides were achieved by [3,3] sigmatropic rearrangement reaction of the disaccharide 13 having a 4-trichloroacetimidate-2-enoside group, prepared in turn by glycosylation of thioglycosyl donors using Pd(CH3CN)2Cl2-AgOTf as a promoter.