doi:10.1016/S0040-4039(01)01427-7
Copyright © 2001 Elsevier Science Ltd All rights reserved.
Facile synthesis of conjugated exo-glycals
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Wen-Bin Yanga, Chung-Yi Wua, Che-Chien Changa, Shwu-Huey Wang†, a, Chin-Fen Teoa and Chun-Hung Lin
, a, 
aInstitute of Biological Chemistry, Academia Sinica, No.128, Academia Road Section 2, Nan-Kang, Taipei, 11529, Taiwan
Received 12 July 2001;
revised 1 August 2001;
accepted 6 August 2001.
Available online 16 August 2001.
Abstract
Two efficient methods were explored for the synthesis of various conjugated exo-glycals: (i) by nucleophilic addition of sugar lactones with a subsequent dehydration, and (ii) by selenylation of C-glycosides with a subsequent selenoxide elimination. These reactions occurred in a stereoselective manner to give exclusively or predominantly the (Z)-isomers of exo-glycals.
Table 1.
Preparation of five conjugated exo-glycals 3a–e via the nucleophilic addition products 2a–e
a Compound
3a existed as a mixture of
Z and
E isomers (5/1). Compounds
3b–
e all have the
Z configuration.
Table 2.
Preparation of five conjugated exo-glycals 6a–e via the condensation products 5a–e
a The formation of compound
5a was not observed. Instead,
6a was directly obtained in the addition reaction.

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† Taipei Medical University.