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.
Autori interni: | |
Autori: | BARILI PL; BERTI G; CATELANI G; COLONNA F; D'ANDREA F |
Titolo: | 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 |
Anno del prodotto: | 1989 |
Digital Object Identifier (DOI): | 10.1016/0008-6215(89)84142-4 |
Appare nelle tipologie: | 1.1 Articolo in rivista |
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