Novel Glycosidation of α-d-Altropyranosides

Takahiro Nakayama; Kazusa Nishiyama; Hideaki Natsugari; Hideyo Takahashi

doi:10.1055/s-0029-1217073

PAPER

Novel Glycosidation of α-d-Altropyranosides

Takahiro Nakayama, Kazusa Nishiyama, Hideaki Natsugari, Hideyo Takahashi*
School of Pharmaceutical Sciences, Teikyo University, Sagamiko, Sagamihara, Kanagawa 229-0195, Japan
Fax: +81(426)853728; e-Mail: hide-tak@pharm.teikyo-u.ac.jp;

Abstract

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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

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References

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