A facile synthesis of (1S,5R,6S)-5-azido-6-benzyloxycyclohex-2-en-1-ol

Takanori Tanaka; Qitao Tan; Kazunari Iwanaga; Masahiko Hayashi

doi:10.1016/j.carres.2010.11.012

A facile synthesis of (1S,5R,6S)-5-azido-6-benzyloxycyclohex-2-en-1-ol

Carbohydr Res. 2011 Feb 1;346(2):340-2. doi: 10.1016/j.carres.2010.11.012. Epub 2010 Nov 19.

Authors

Takanori Tanaka¹, Qitao Tan, Kazunari Iwanaga, Masahiko Hayashi

Affiliation

¹ Department of Chemistry, Graduate School of Science, Kobe University, Kobe 657-8501, Japan.

PMID: 21163468
DOI: 10.1016/j.carres.2010.11.012

Abstract

A facile and short synthesis of (1S,5R,6S)-5-azido-6-benzyloxycyclohex-2-en-1-ol (1) has been achieved in high yield starting from 4,5-epoxycyclohex-1-ene by using a catalytic asymmetric allylic oxidation reaction.

Publication types

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

MeSH terms

Azides / chemical synthesis*
Cyclohexanes / chemistry
Cyclohexanols / chemical synthesis*
Enzyme Inhibitors / chemical synthesis*
Enzyme Inhibitors / pharmacology
Epoxy Compounds / chemistry
Glycoside Hydrolases / antagonists & inhibitors*

Substances

4,5-epoxycyclohexene
Azides
Cyclohexanes
Cyclohexanols
Enzyme Inhibitors
Epoxy Compounds
Glycoside Hydrolases