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Direct and Stereoselective Synthesis of 2‐Acetamido‐2‐deoxy‐β‐ D ‐glycopyranosides by Using the Phosphite Method
Author(s) -
Arihara Ryoichi,
Nakamura Seiichi,
Hashimoto Shunichi
Publication year - 2005
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200461988
Subject(s) - stereoselectivity , chemistry , imide , stereochemistry , medicinal chemistry , organic chemistry , catalysis
Avoiding the intermediate : The β‐selective glycosidation of 2‐acetamido‐2‐deoxyglycosyl diethyl phosphites promoted by bis(trifluoromethanesulfonyl)imide (Tf 2 NH) proceeds in a direct manner and does not afford an oxazolinium ion as an intermediate (see scheme; MS (4Å)=4‐Å molecular sieves).