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NAP Ether Mediated Intramolecular Aglycon Delivery: A Unified Strategy for 1,2‐ cis ‐Glycosylation (Eur. J. Org. Chem. 25/2008)
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.200890066
Subject(s) - chemistry , nap , intramolecular force , glycosylation , stereochemistry , stereospecificity , glycosyl donor , ether , stereoselectivity , acetal , glycosyl , organic chemistry , catalysis , biochemistry , neuroscience , biology
The cover picture shows shows the general outline for 2‐naphthylmethyl (NAP) ether mediated intramolecular aglycon delivery (NAP‐IAD). The initial formation of the mixed acetal ( MA ) from the NAP ether protected glycosyl donor ( D ) having the manno ‐ or gluco ‐configuration at the C2 position and the glycosyl acceptor ( A ), followed by stereoselective intramolecular glycosylation, afforded the desired 1,2‐ cis glycoside in high yield. Stereospecific constructions of various 1,2‐ cis linkages, such as β‐mannopyrano‐, β‐arabinofurano‐ and α‐glucopyranosides, were achieved through NAP‐IAD. Details are discussed in the article by A. Ishiwata, Y. Munemura and Y. Ito on p. 4250 ff.