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Stereoselective Synthesis of the Core Structure of the Nephritogenoside Glycopeptide

✍ Scribed by Zhang, Hong ;Wang, Yali ;Thürmer, René ;Meisenbach, Mark ;Voelter, Wolfgang

Publisher: John Wiley and Sons
Year: 1997
Tongue: English
Weight: 742 KB
Volume: 1997
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199719970910

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✦ Synopsis

Abstract

A new strategy for the construction of the O‐glycoside bond in the nephritogenoside unit using the phenylsulfenyl method is reported. The readily accessible phenylsulfinyl glycoside proved to be an excellent glycosyl donor, leading to high yields and good selectivity. The extremely mild conditions utilized in glycosylation reactions allow trityl and other sensitive protecting groups to be used for temporary protection. The fact that phenyl thioglycosides function as glycosyl acceptors during the coupling reaction and can easily be transformed into glycosyl donors by conversion to phenylsulfinyl glycosides, enables complex oligosaccharides to be prepared in a highly convenient manner.

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