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Convenient Synthesis of Bicyclic Carbohydrate 1,2‐Lactones and Their Stereoselective Opening to 1‐Functionalized Glucose Derivatives
Author(s) -
Yin Jian,
Linker Torsten
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200802178
Subject(s) - stereoselectivity , decarboxylation , carbohydrate , chemistry , bicyclic molecule , anomer , stereochemistry , organic chemistry , combinatorial chemistry , catalysis
Closed and re‐opened for business : C‐2 branched carbohydrates 1 cyclize under conditions of decarboxylation to the hitherto unknown carbohydrate 1,2‐lactones 2 in high yields. The gluco isomer can be opened at the anomeric position with various nuceophiles in the presence of Sc(OTf) 3 , which allows the stereoselective synthesis of 1‐functionalized glucose derivatives 3 . Thus, 1,2‐ bis‐C ‐branched saccharides become available in only a few steps starting from glycals.