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Dialkylphosphates as Stereodirecting Protecting Groups in Oligosaccharide Synthesis
Author(s) -
Yamada Takeshi,
Takemura Kazunobu,
Yoshida Junichi,
Yamago Shigeru
Publication year - 2006
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.200602699
Subject(s) - chemistry , protecting group , glycosylation , anomer , oligosaccharide , glycosyl , phosphoric acid , stereochemistry , organic chemistry , biochemistry , alkyl
Double duty : A phosphoric ester at the C2 position in glycosyl donors directs the glycosylation to occur selectively at the anomeric carbon atom with complete 1,2‐ trans selectivity. Since the phosphoric ester can be removed to give the hydroxy function, this group serves as a stereodirecting protecting group in oligosaccharide synthesis.