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Elaboration of Monoarabinofuranosidic Building Blocks
Author(s) -
Sanchez Sylvie,
Bamhaoud Toufiq,
Prandi Jacques
Publication year - 2002
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 - 10.1002/1099-0690(200211)2002:22<3864::aid-ejoc3864>3.0.co;2-8
Subject(s) - chemistry , lewis acids and bases , ethanethiol , nucleophile , glycosidic bond , stereoselectivity , thio , glycosylation , catalysis , organic chemistry , lewis acid catalysis , stereochemistry , combinatorial chemistry , biochemistry , enzyme
Nucleophilic opening of 1,2,5‐orthoesters 1 , 2 and 6 of D ‐arabinose with alcohols, ethanethiol and selenophenol was carried out under very mild conditions with Lewis acid catalysis. The reaction is stereoselective and gave α‐ D ‐arabinofuranosides in high yields. Various monoarabinofuranosides, thio‐ and selenoglycoside donors as well as acceptors were obtained in few steps from the opening products. These building blocks define a comprehensive system of glycosylation for the synthesis of any glycosidic linkage between arabinofuranosides. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)