Novel Glycosidation of α-d-Altropyranosides

Abstract

A new glycosidation of α-d-altropyranosides, in which the 2-hydroxy group is not protected, was developed. The reaction proceeds via a 1,2-β-oxirane, which is formed in situ without extra steps for exchanging the 1-methoxy group to a more reactive leaving group. The glycoside bond of α-d-altropyranoside was shown to be weaker compared with those of α-d-glucopyranoside and α-d-mannopyranoside.

Key words

carbohydrates - glycosylations - epoxides - ring opening - d-altropyranoside

References

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8

Glycosidation of 2-alkylated altrosides resulted in lower yields.