Regioselective synthesis of 4azido-Neu2en5,7Ac(2)1Me and its intramolecular transformation to 4azido-Neu2en5,9Ac(2)1Me

Qingjie Zhao; Yuanyuan Lou; Ruisheng Xiong; Haihong Li; Jingshan Shen

doi:10.1016/j.carres.2008.06.016

Regioselective synthesis of 4azido-Neu2en5,7Ac(2)1Me and its intramolecular transformation to 4azido-Neu2en5,9Ac(2)1Me

Carbohydr Res. 2008 Sep 22;343(14):2459-62. doi: 10.1016/j.carres.2008.06.016. Epub 2008 Jun 20.

Authors

Qingjie Zhao¹, Yuanyuan Lou, Ruisheng Xiong, Haihong Li, Jingshan Shen

Affiliation

¹ Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, PR China.

PMID: 18635158
DOI: 10.1016/j.carres.2008.06.016

Abstract

Methyl 5-N-acetyl-7-O-acetyl-4-azido-2,3-didehydro-2,4-dideoxy-neuraminic acid (4azido-Neu2en5,7 Ac(2)1Me) was synthesized regioselectively starting from 4azido-Neu2en5Ac1Me in high yield. The transformation of 4azido-Neu2en5,7Ac(2)1Me to the corresponding thermodynamically stable 4azido-Neu2en5,9Ac(2)1Me via intramolecular acetyl migration was confirmed by single-crystal X-ray diffraction analysis. The proposed rearrangement mechanism is discussed.

Publication types

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

MeSH terms

Carbohydrate Conformation
Carbohydrates / chemical synthesis*
Carbohydrates / chemistry*
Crystallography, X-Ray
Hydrolysis
Models, Molecular
N-Acetylneuraminic Acid / analogs & derivatives*
N-Acetylneuraminic Acid / chemical synthesis
N-Acetylneuraminic Acid / chemistry

Substances

Carbohydrates
methyl 5-N-acetyl-7-O-acetyl-4-azido-2,3-didehydro-2,4-dideoxyneuraminic acid
methyl 5-acetamido-9-O-acetyl-2,6-anhydro-4-azido-3,4,5-trideoxy-glycero-galacto-non-2-enoic acid
N-Acetylneuraminic Acid