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Simple Synthesis of KDO α‐Glycosides by Anomerically Selective O ‐Alkylation
Author(s) -
Schmidt Richard R.,
Esswein Angelika
Publication year - 1988
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198811781
Subject(s) - alkylation , glycoside , deprotonation , adduct , chemistry , stereochemistry , organic chemistry , combinatorial chemistry , catalysis , ion
Oligosaccharides with the α(2–6′)‐bound oxodeoxysugar KDO play an exceptionally large role as components of lipopolysacharides. The synthesis of such KDO‐α‐glycosides has now been accomplished in high yields with the key adduct 1 . The trick is the reaction with NaH resulting in double deprotonation to a chelate in which the α‐configuration is “fixed”.