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Oxydations et halogénations régiosélectives et réactions carbéniques de dérivés de sucres portant un groupement thioéther

✍ Scribed by Jean M. J. Tronchet; Hansjörg Eder

Publisher
John Wiley and Sons
Year
1980
Tongue
German
Weight
821 KB
Volume
63
Category
Article
ISSN
0018-019X

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✦ Synopsis

Regioselective Oxidations, Regioselective Halogenations and Carbene Reactions of Sugar Derivatives Bearing a Thioether Group

Regioselective stoechiometrically controlled procedures are described for the oxidation of thiosugars either at the sulfur atom (to sulfoxides or sulfones) or at a hydroxymethylene group (to ketosugars). Ruthenium tetraoxide reacted at both sites. Chloration (SO~2~Cl~2~) of β‐ketothioether sugar derivative 3 took place exclusively at C(6). Evidence is given that a chlorosulfonium intermediate C was formed when the dichloroketothiosugar derivative 6 was treated with SO~2~Cl~2~. The carbene generated from the tosylhydrazone 16 rearranged to the enoses 17–20, the migrating group coming in equal proportions from C(4) and C(6). Some stereochemical aspects of these reactions are discussed.

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