Efficient synthesis of sugar oxazolines from unprotected N-acetyl-2-amino sugars by using chloroformamidinium reagent in water

Masato Noguchi; Tomonari Tanaka; Hidetoshi Gyakushi; Atsushi Kobayashi; Shin-ichiro Shoda

doi:10.1021/jo8024708

Efficient synthesis of sugar oxazolines from unprotected N-acetyl-2-amino sugars by using chloroformamidinium reagent in water

J Org Chem. 2009 Mar 6;74(5):2210-2. doi: 10.1021/jo8024708.

Authors

Masato Noguchi¹, Tomonari Tanaka, Hidetoshi Gyakushi, Atsushi Kobayashi, Shin-ichiro Shoda

Affiliation

¹ Department of Biomolecular Engineering, Graduate School of Engineering, Tohoku University, 6-6-11-514 Aoba, Aramaki Aobaku, Sendai, Japan.

PMID: 19203234
DOI: 10.1021/jo8024708

Abstract

Sugar oxazoline derivatives were directly synthesized from the corresponding N-acetyl-2-amino sugars in aqueous media by using a chloroformamidinium-type dehydrating reagent. The present method could successfully be applied to chito-oligosaccharides, saccharides with acid functions, and a complex-type oligosaccharide derived from a glycopeptide.

Publication types

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

MeSH terms

Carbohydrates / chemistry*
Formamides / chemistry*
Molecular Structure
Oxazoles / chemical synthesis*
Oxazoles / chemistry
Water / chemistry*

Substances

Carbohydrates
Formamides
Oxazoles
Water