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Rapid Assembly of Oligosaccharides: Total Synthesis of a Glycosylphosphatidylinositol Anchor of Trypanosoma brucei
Author(s) -
Baeschlin Daniel K.,
Chaperon André R.,
Charbonneau Virginie,
Green Luke G.,
Ley Steven V.,
Lücking Ulrich,
Walther Eric
Publication year - 1998
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/(sici)1521-3773(19981231)37:24<3423::aid-anie3423>3.0.co;2-i
Subject(s) - desymmetrization , dihydropyran , chemistry , oligosaccharide , protecting group , inositol , glycosylation , biochemistry , stereochemistry , organic chemistry , enantioselective synthesis , receptor , catalysis , alkyl
Six building blocks, six reaction steps : The recently developed innovative methodology facilitated the convergent synthesis of the complex oligosaccharide core 1 (shown here with protecting groups) for the total synthesis of a glycosylphosphatidylinositol (GPI) anchor. The key factors are the tuning of the reactivity of the building blocks by using 1,2‐diacetal protecting groups and the desymmetrization of glycerol and myo ‐inositol with a chiral bis(dihydropyran).