用四硫代钼酸盐将端基叠氮化物选择性还原为胺：β-D-糖基胺的合成

Selective reduction of anomeric azides to amines with tetrathiomolybdate: synthesis of beta-D-glycosylamines.

作者信息

Sridhar Perali Ramu, Prabhu Kandikere Ramaiah, Chandrasekaran Srinivasan

机构信息

Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, Karnataka, India.

出版信息

J Org Chem. 2003 Jun 27;68(13):5261-4. doi: 10.1021/jo0266947.

DOI:10.1021/jo0266947

PMID:12816487

Abstract

A number of beta-d-glycosyl azide derivatives undergo reduction on treatment with tetrathiomolybdate to produce the corresponding beta-d-glycosylamines exclusively without anomerization under very mild and neutral reaction conditions. Acetyl, allyl, benzoyl, and benzyl protective groups are left untouched under the reaction conditions. An exclusive selectivity in the reduction of anomeric azides is observed, while the C-2 and C-6 azides are left untouched.

摘要

一些β-D-糖基叠氮衍生物在与四硫代钼酸盐反应时会发生还原反应，在非常温和的中性反应条件下仅生成相应的β-D-糖基胺，且不会发生异头化。乙酰基、烯丙基、苯甲酰基和苄基保护基在反应条件下不受影响。在还原异头叠氮化物时观察到了专一的选择性，而C-2和C-6叠氮化物则不受影响。