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. 2002 Aug 16;337(14):1319-24.
doi: 10.1016/s0008-6215(02)00124-6.

Preparation of orthogonally protected chitosan oligosaccharides: observation of an anomalous remote substituent effect

Siong-Tern Liew  1 , Alexander Wei
Affiliations

Preparation of orthogonally protected chitosan oligosaccharides: observation of an anomalous remote substituent effect

Siong-Tern Liew et al. Carbohydr Res. .

Abstract

Orthogonally protected chitosan tetrasaccharides were synthesized in a convergent fashion by trichloroacetimidate activation. The anomeric substituent at the reducing end of the disaccharide acceptor has a remarkably strong influence on glycosidic coupling; a thiophenyl-substituted disaccharide was observed to be an unusually poor glycosyl acceptor in comparison with the corresponding allyloxy-substituted disaccharide.

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