Treatment of O-protected 3,4-0-isopropylidene-beta-galactopyranosides with tert-BuOK in N,N-dimethylformamide or methyl sulfoxide produces 4-deoxy-a-Lthree- hex-4-enopyranosides in good yields. The corresponding a-anomers and the non-O-protected derivatives are resistant to this treatment. Reaction of methyl 4- deoxy-2,6-di-O-methyl-alfa-L-threo-hex-4-enopyranoside with 3-chloroperbenzoic acid in CH2Cl2 gave a crystalline adduct that was hydrolyzed to 2,6-di-O-methyl-LaraBino- hexos-5-ulose.

A FACILE CONVERSION OF 3,4-O-ISOPROPYLIDENE-BETA-D-GALACTOPYRANOSIDES INTO 4-DEOXY-ALPHA-L-THREO-HEX-4-ENOPYRANOSIDE AND L-ARABINO-HEXOS-5-ULOSE DERIVATIVES

CATELANI, GIORGIO;D'ANDREA, FELICIA
1989

Abstract

Treatment of O-protected 3,4-0-isopropylidene-beta-galactopyranosides with tert-BuOK in N,N-dimethylformamide or methyl sulfoxide produces 4-deoxy-a-Lthree- hex-4-enopyranosides in good yields. The corresponding a-anomers and the non-O-protected derivatives are resistant to this treatment. Reaction of methyl 4- deoxy-2,6-di-O-methyl-alfa-L-threo-hex-4-enopyranoside with 3-chloroperbenzoic acid in CH2Cl2 gave a crystalline adduct that was hydrolyzed to 2,6-di-O-methyl-LaraBino- hexos-5-ulose.
Barili, Pl; Catelani, Giorgio; Catelani, G; Colonna, F; D'Andrea, Felicia
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11568/204120
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