Premium
Direct, Mild, and Selective Synthesis of Unprotected Dialdo‐Glycosides
Author(s) -
Angelin Marcus,
Hermansson Magnus,
Dong Hai,
Ramström Olof
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600288
Subject(s) - chemistry , glycoside , imine , combinatorial chemistry , trichloroisocyanuric acid , organic chemistry , catalysis
A direct and highly convenient organocatalytic method for the preparation of 1,5‐dialdo‐pyranosides and 1,4‐dialdo‐furanosides is presented. The method relies on the chemoselective properties of TEMPO in combination with trichloroisocyanuric acid under very mild, basic conditions. Unprotected glycosides are prepared in a single step in high yields and are efficiently purified with the use of solid‐phase imine capture. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)