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
1989-01-01
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.File in questo prodotto:
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