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New syntheses of methyl 5-thio-β-d-arabinopyranoside and (+)-biotin

✍ Scribed by Neil A. Hughes; Ksenija-Maria Kuhajda; Dusan A. Miljkovic

Publisher: Elsevier Science
Year: 1994
Tongue: English
Weight: 436 KB
Volume: 257
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(94)80043-x

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✦ Synopsis

Previously one of us reported 121 that methyl 3,4-0-isopropylidene-2-Omethanesulfonyl-5.thio-~-D-~~pyranoside (1) readily unde~ent ring ~ntra~tion in methanol to give 2,5-dideo~-2,5-epithio-o-arabinose dimethyl acetal (2). It was of interest to examine this reaction with the corresponding D-arabinose derivative 3 because the expected product 4 is a potential precursor for a new synthesis of (-I-)-biotin (5). A number of syntheses of 5 from monosaccharides have been reported previously, e.g., also from D-arabinose [3,4], from o-glucose [5,6], and from D-mannose [7f.

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