Title

Application of bis(diphenylphosphino)ethane (DPPE) in Staudinger-type N-glycopyranosyl amide synthesis.

Document Type

Article

Publication Date

July 2006

Abstract

Bis(diphenylphosphino)ethane (DPPE) reacts with pyranosyl azides derived from d-glucose and d-glucuronic acid in the presence of acid chlorides to yield the corresponding glycosyl amides. Reaction rates are comparable to those with triphenylphosphine, however, the byproduct phosphine oxide is easily removed from reaction mixtures using column chromatography. The simple and clean workup allows for the formation of collections of related compounds by parallel synthesis, and the method is also applicable to scaled-up reactions. The β-stereochemistry of the glycosyl azide precursor is retained in all cases, which is supported by X-ray crystallography in several cases.

Journal

Carbohydrate Research

Volume

341

Issue

10

First Page

1645

Last Page

1656

Share

COinS