Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
1388875 | Carbohydrate Research | 2007 | 6 Pages |
Abstract
C-6 opening of 5,6-cyclic sulfate derivatives of mannofuranose with a thiolate anion followed by acidic hydrolysis of the acyclic sulfate gave 6-S-alkyl derivatives in good yields (70–95%) and short reaction times (10–15 min). This methodology was applied to the synthesis of methyl 2,3-O-isopropylidene-6-S-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl)-6-thio-α-d-mannofuranoside (70%), 2,3-O-isopropylidene-6-S-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl)-6-thio-α-d-mannofuranose (87%) and 2,3-O-isopropylidene-6-S-(1,2:3,4-di-O-isopropylidene-α-d-galactopyranos-6-yl)-6-thio-α-d-mannofuranose (87%).
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Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Anne Wadouachi, Ludivine Lescureux, David Lesur, Daniel Beaupère,