Kinetically controlled reaction of 4.5 equiv. of 2-methoxypropene with some alkyl α- and β-d-galactopyranosides gave the 2,3:4,6-di-O-isopropylidene derivatives in high yields (80-85%). With 2 equiv. of 2-methoxypropene, benzyl β-d-galactopyranoside gave the 4,6- and the 3,4-monoacetals in the ratio 30:1 together with ∼20% of the 2,3:4,6-diacetal. The structures of methyl 2,3:4,6-di-O-isopropylidene-α- and -β-d-galactopyranosides were determined by X-ray analysis. The former crystallised in the orthorhombic system, P212121, with a = 5.503, b = 16.105, c = 16.822 Å, and Z = 4, the latter in the monoclinic system, P21, with a = 10.400, b = 13.344, c = 11.647 Å, β = 111.50, and Z = 4. The α anomer and the two molecules of the β anomer had the d-galactopyranoside and the 1,3-dioxane rings in twist-chair conformations and the dioxolane ring in a half-chair conformation. N.m.r. spectroscopy suggested the occurrence of similar conformations in solution.

SYNTHESIS OF 2,3-4,6-DI-O-ISOPROPYLIDENE DERIVATIVES OF ALKYL-ALPHA-GALACTOPYRANOSIDES AND ALKYL-BETA-D-GALACTOPYRANOSIDES, AND ELUCIDATION OF STRUCTURE BY NMR AND X-RAY-ANALYSIS

CATELANI, GIORGIO;
1988

Abstract

Kinetically controlled reaction of 4.5 equiv. of 2-methoxypropene with some alkyl α- and β-d-galactopyranosides gave the 2,3:4,6-di-O-isopropylidene derivatives in high yields (80-85%). With 2 equiv. of 2-methoxypropene, benzyl β-d-galactopyranoside gave the 4,6- and the 3,4-monoacetals in the ratio 30:1 together with ∼20% of the 2,3:4,6-diacetal. The structures of methyl 2,3:4,6-di-O-isopropylidene-α- and -β-d-galactopyranosides were determined by X-ray analysis. The former crystallised in the orthorhombic system, P212121, with a = 5.503, b = 16.105, c = 16.822 Å, and Z = 4, the latter in the monoclinic system, P21, with a = 10.400, b = 13.344, c = 11.647 Å, β = 111.50, and Z = 4. The α anomer and the two molecules of the β anomer had the d-galactopyranoside and the 1,3-dioxane rings in twist-chair conformations and the dioxolane ring in a half-chair conformation. N.m.r. spectroscopy suggested the occurrence of similar conformations in solution.
Barili, Pl; Catelani, Giorgio; Colonna, F; Marra, A; Cerrini, S; Lamba, D.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11568/10544
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