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Synthesis 1996; 1996(3): 341-348
DOI: 10.1055/s-1996-4219
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Synthesis of 2-Amino-2-deoxy-D-hexopyranoside-Containing Disaccharides Involving Glycosylation and [3,3] Sigmatropic Rearrangement

Kazuyoshi Takeda* , Eisuke Kaji, Hiroko Nakamura, Akira Akiyama, Yaeko Konda, Yoshihisa Mizuno, Hiroaki Takayanagi, Yoshihiro Harigaya
  • *Department of Chemistry, School of Science, Kitasato University, 1-15-1, Kitasato, Sagamihara-shi, Kanagawa 228, Japan, Fax +81(427)789400
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Publication Date:
31 December 2000 (online)

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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.

2-amino-2-deoxy-D-hexopyranosides - [3,3]-Sigmatropy - O-glycosylation - S-glycoside - Pd(CH3CN)2Cl2/QgOTf