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A Streamlined Strategy for Aglycone Assembly and Glycosylation
Author(s) -
Partridge Katherine M.,
Bader Scott J.,
Buchan Zachary A.,
Taylor Christopher E.,
Montgomery John
Publication year - 2013
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.201307680
Subject(s) - aglycone , glycosylation , chemistry , intramolecular force , glycosyl , combinatorial chemistry , aldehyde , alkyne , stereochemistry , catalysis , organic chemistry , biochemistry , glycoside
Multipurpose sugars : Carbohydrate‐derived silane reagents are utilized as the reductant for nickel‐catalyzed aldehyde–alkyne reductive coupling reactions and as the glycosyl donor for subsequent intramolecular glycosylation. The approach enables the assembly of the carbon–carbon framework and stereochemical features of an aglycone while simultaneously establishing the site of glycosylation.