Premium
Stereoselective Synthesis of the Core Structure of the Nephritogenoside Glycopeptide
Author(s) -
Zhang Hong,
Wang Yali,
Thürmer René,
Meisenbach Mark,
Voelter Wolfgang
Publication year - 1997
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719970910
Subject(s) - chemistry , glycosyl , glycosylation , glycoside , stereoselectivity , glycosyl donor , combinatorial chemistry , selectivity , organic chemistry , catalysis , biochemistry
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.