1,2-Dideoxy-3,4:5,7-bis-O-(1-methylethylidene)-D-gluco- and D-galacto-hept-l-ynitols were synthesized starting respectively from benzyl α,β-D-glucopyranoside and from benzyl α,β-D-galactopyranoside by bis-acetonidation, hydrogenolysis, Wittig reaction with chloromethylenetriphenylphosphorane, and dehydrohalogenation. The structures of the obtained compounds were confirmed by the NMR spectrocopic data which also allowed to determine the conformations of the molecules.
1,2-Dideoxy-3,4-5,7-Bis-O-(1-Methylethylidene)-D-Gluco And D-Galacto-Hept-1-Ynitols - Synthesis And Conformational Studies / M. Mella, L. Panza, F. Ronchetti, L. Toma. - In: TETRAHEDRON. - ISSN 0040-4020. - 44:6(1988), pp. 1673-1678. [10.1016/S0040-4020(01)86729-6]
1,2-Dideoxy-3,4-5,7-Bis-O-(1-Methylethylidene)-D-Gluco And D-Galacto-Hept-1-Ynitols - Synthesis And Conformational Studies
F. RonchettiPenultimo
;
1988
Abstract
1,2-Dideoxy-3,4:5,7-bis-O-(1-methylethylidene)-D-gluco- and D-galacto-hept-l-ynitols were synthesized starting respectively from benzyl α,β-D-glucopyranoside and from benzyl α,β-D-galactopyranoside by bis-acetonidation, hydrogenolysis, Wittig reaction with chloromethylenetriphenylphosphorane, and dehydrohalogenation. The structures of the obtained compounds were confirmed by the NMR spectrocopic data which also allowed to determine the conformations of the molecules.
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