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NAP Ether Mediated Intramolecular Aglycon Delivery: A Unified Strategy for 1,2‐ cis ‐Glycosylation
Author(s) -
Ishiwata Akihiro,
Munemura Yuichi,
Ito Yukishige
Publication year - 2008
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.200800249
Subject(s) - chemistry , nap , intramolecular force , glycosylation , stereospecificity , stereochemistry , stereoselectivity , ether , organic chemistry , catalysis , biochemistry , neuroscience , biology
A methodology directed towards the stereoselective construction of 1,2‐ cis ‐glycosides through naphthylmethyl (NAP) ether mediated intramolecular aglycon derivery (IAD) has been developed. Stereospecific constructions of various 1,2‐ cis linkages, as in β‐mannopyrano‐, β‐arabinofurano‐, and α‐glucopyranosides, were achieved through NAP‐IAD. This methodology was successfully applied to the synthesis of Glcα(1→2)‐Glcα(1→3)‐Glcα(1→3)Man (Glc 3 Man 1 ), the nonreducing terminal structure of the tetradecasaccharide Glc 3 Man 9 GlcNAc 2 , a common precursor of all N ‐linked glycans.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)