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Synthesis of the trisaccharide moiety and a cholesteryl analog of phyteumosides

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Title Synthesis of the trisaccharide moiety and a cholesteryl analog of phyteumosides
 
Creator ADAK, S
EMMADI, M
KULKARNI, SS
 
Subject CARBOHYDRATE-CHEMISTRY
SILYL
DERIVATIVES
MIGRATION
FACILE
 
Description A first synthesis of the trisaccharide moiety of the phyteumosides and its cholesteryl analog is described using easily accessible and regioselectively protected D-glucose, L-rhamnose and D-galactose building blocks via a linear glycosylation approach. The two glycosyl donors were prepared as thiophenyl (SPh) glycosides. Trichloroacetimidate (TCAl) coupling was employed for the first glycosylation step while thioglycoside activation was used for the second glycosylation to assemble the O-allyl trisaccharide. After removal of the anomeric allyl group, the trisaccharide was converted into a TCAl donor. Using cholesterol as an acceptor in combination with acetonitrile as a participating solvent to achieve beta-selectivity in glycosylation, a phyteumoside analog was obtained.
 
Publisher ROYAL SOC CHEMISTRY
 
Date 2014-12-29T06:04:18Z
2014-12-29T06:04:18Z
2014
 
Type Article
 
Identifier RSC ADVANCES, 4(15)7611-7616
2046-2069
http://dx.doi.org/10.1039/c3ra47523a
http://dspace.library.iitb.ac.in/jspui/handle/100/17264
 
Language English