A facile preparation of uronates via selective oxidation with TEMPO/KBr/Ca(OCl)(2) under aqueous conditions

Feng Lin; Wenjie Peng; Wen Xu; Xiuwen Han; Biao Yu

doi:10.1016/j.carres.2004.02.001

A facile preparation of uronates via selective oxidation with TEMPO/KBr/Ca(OCl)(2) under aqueous conditions

Carbohydr Res. 2004 Apr 28;339(6):1219-23. doi: 10.1016/j.carres.2004.02.001.

Authors

Feng Lin¹, Wenjie Peng, Wen Xu, Xiuwen Han, Biao Yu

Affiliation

¹ State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China.

PMID: 15063215
DOI: 10.1016/j.carres.2004.02.001

Abstract

Addition of solid Ca(OCl)(2) as the terminal oxidant in the TEMPO-mediated selective oxidation has the benefit of easier operation. A variety of partially protected saccharide derivatives (1a-l) have been successfully converted into the corresponding uronate derivatives, including disaccharide building blocks for GAG fragments and precursors to saponins. The beneficial effect of Aliquat 336 was also disclosed in the oxidation of certain substrates.

Publication types

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

MeSH terms

Bromides / chemistry*
Calcium Compounds / chemistry*
Carbohydrate Conformation
Carbohydrate Sequence
Chromatography
Cyclic N-Oxides / chemistry*
Models, Chemical
Molecular Sequence Data
Oxygen / chemistry
Potassium Compounds / chemistry*
Saponins / chemistry
Sodium Hypochlorite / chemistry
Time Factors
Uronic Acids / chemistry*
Water / chemistry

Substances

Bromides
Calcium Compounds
Cyclic N-Oxides
Potassium Compounds
Saponins
Uronic Acids
Water
calcium hypochlorite
Sodium Hypochlorite
potassium bromide
Oxygen
TEMPO