Stereospecific synthesis of the alpha- and beta-D-glucopyranosyl ureas

Y Ichikawa; T Nishiyama; M Isobe

doi:10.1021/jo0100751

Stereospecific synthesis of the alpha- and beta-D-glucopyranosyl ureas

J Org Chem. 2001 Jun 15;66(12):4200-5. doi: 10.1021/jo0100751.

Authors

Y Ichikawa¹, T Nishiyama, M Isobe

Affiliation

¹ Laboratory of Organic Chemistry, School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan. ichikawa@agr.nagoya-u.ac.jp

PMID: 11397154
DOI: 10.1021/jo0100751

Abstract

A new, one-pot, two-stage procedure for the preparation of the alpha- and beta-D-glucopyranosyl ureas has been developed. Oxidation of glucopyranosyl isocyanides provides glucopyranosyl isocyanates, which can be trapped in situ with amines to afford good yields of glucopyranosyl ureas. Application of this method establishes the successful synthesis of the hitherto unknown N,N'-di-alpha,alpha- and alpha,beta-D-glucopyranosyl ureas.