One-pot alpha-glycosylation method using Appel agents in N,N-dimethylformamide

Yoshihiro Nishida; Yuko Shingu; Hirofumi Dohi; Kazukiyo Kobayashi

doi:10.1021/ol034269+

One-pot alpha-glycosylation method using Appel agents in N,N-dimethylformamide

Org Lett. 2003 Jul 10;5(14):2377-80. doi: 10.1021/ol034269+.

Authors

Yoshihiro Nishida¹, Yuko Shingu, Hirofumi Dohi, Kazukiyo Kobayashi

Affiliation

¹ Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa-ku, Nagoya 464-8603, Japan. nishida@mol.nagoya-u.ac.jp

PMID: 12841734
DOI: 10.1021/ol034269+

Abstract

[reaction: see text] A concept for the development of practical glycosylation is presented and demonstrated by one-pot alpha-glycosylation applying Appel agents for 2-O-benzyl-1-OH hexoses in DMF. The reaction, in situ giving the equilibrium of glycosyl bromides and more reactive O-glycoside intermediates, accomplishes a near-quantitative alpha-glycosylation removing the water molecules.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Dimethylformamide / chemistry*
Glycosylation

Substances

Dimethylformamide