Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
1389048 | Carbohydrate Research | 2008 | 5 Pages |
Abstract
An efficient synthesis of 4-methoxyphenyl α-l-Rhap-(1â3)-α-l-Rhap-(1â3)-α-l-Rhap-(1â2)-6-deoxy-α-l-Talp, the tetrasaccharide related to the GPLs of Mycobacterium intracellare serotype 7, was achieved with 4-methoxyphenyl 3,4-di-O-benzoyl-6-deoxy-α-l-talopyranoside (6c) as the key intermediate which was obtained through selective 3-O-benzoylation of 4-O-benzoyl-6-deoxy-α-l-taloside. Coupling of 6c with 3-O-allyloxycarbonyl-2,4-di-O-benzoyl-α-l-rhamnopyranosyl trichloroacetimidate followed by removal of the allyloxycarbonyl protecting group afforded the disaccharide acceptor 11. Condensation of 11 with 2,3,4-tri-O-benzoyl-α-l-rhamnopyranosyl-(1â3)-2,4-di-O-benzoyl-α-l-rhamnopyranosyl trichloroacetimidate and subsequent deprotection gave the target tetrasaccharide.
Related Topics
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Authors
Shiqiang Yan, Xiaomei Liang, Peiyu Diao, Ye. Yang, Jianjun Zhang, Daoquan Wang, Fanzuo Kong,