Issue 9, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Synthesis of a group of diosgenyl saponins with combined use of glycosyl trichloroacetimidate and thioglycoside donors

Hai Yu,b   Biao Yu,*a   Xiangyang Wu,a   Yongzheng Hui*a  and  Xiuwen Hanb  

* Corresponding authors

a State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai

b State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, China

Abstract

With the combined use of glycosyl trichloroacetimidates and thioglycosides, a group of natural diosgenyl saponins (1–6) are efficiently synthesized, in either a stepwise or a ‘one-pot’ manner. The trichloroacetimidate is employed as an efficient temporary hydroxy protecting group in glycosylation with the glycosyl trichloroacetimidate. The intermolecular alkylthio-group transfer is demonstrated to be a common side-reaction during glycosylation with thioglycosides.

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Article information

DOI
https://doi.org/10.1039/A909218H
Article type
Paper
Submitted
22 Nov 1999
Accepted
02 Mar 2000
First published
18 Apr 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 1445-1453

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Synthesis of a group of diosgenyl saponins with combined use of glycosyl trichloroacetimidate and thioglycoside donors

H. Yu, B. Yu, X. Wu, Y. Hui and X. Han, J. Chem. Soc., Perkin Trans. 1, 2000, 1445 DOI: 10.1039/A909218H

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