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N ‐Glycosyl Amides: Removal of the Anomeric Protecting Group and Conversion into Glycosyl Donors
Author(s) -
Pleuss Norbert,
Kunz Horst
Publication year - 2003
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.200351351
Subject(s) - glycosyl , oxidizing agent , amide , anomer , chemistry , protecting group , reactivity (psychology) , carbohydrate , glycoside , organic chemistry , combinatorial chemistry , medicine , alkyl , alternative medicine , pathology
Reactivity upon demand : Because of their stability towards acids, bases, and many oxidizing and reducing agents, N ‐glycosyl amides 1 (see scheme) can be used as anomerically protected carbohydrates. The amide function can be cleaved under mild conditions with Ph 3 P/CBr 4 and the carbohydrate activated for the synthesis of N‐ and O‐glycosides 2 . PG=protecting group.