Issue 19, 2006
From the journal:

Organic & Biomolecular Chemistry

Polyhydroxylated homoazepanes and 1-deoxy-homonojirimycin analogues: synthesis and glycosidase inhibition study†

Shankar D. Markad,a   Narayan S. Karanjule,a   Tarun Sharma,b   Sushma G. Sabharwalb  and  Dilip D. Dhavale*a  

* Corresponding authors

a Garware Research Centre, Department of Chemistry, University of Pune, Pune, India
E-mail: ddd@chem.unipune.ernet.in
Fax: +91-20-2569-1728
Tel: +91-20-2560-1225-584

b Division of Biochemistry, Department of Chemistry, University of Pune, Pune, India

Abstract

The Johnson–Claisen rearrangement of D-gluco and L-ido-derived allylic orthoesters afforded γ,δ-unsaturated ester that on ester reduction, epoxidation, regioselective oxirane opening by sodium azide and hydrogenation led to sugar amino alcohols—immediate precursors for 1-deoxy-homonojirimycin 3a,b and polyhydroxylated homoazepanes 4a,b. Our synthetic approach and glycosidase inhibitory activity is reported.

Graphical abstract: Polyhydroxylated homoazepanes and 1-deoxy-homonojirimycin analogues: synthesis and glycosidase inhibition study

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/B609000A
Article type
Paper
Submitted
26 Jun 2006
Accepted
07 Aug 2006
First published
22 Aug 2006

Org. Biomol. Chem., 2006,4, 3675-3680

Permissions

Request permissions

Polyhydroxylated homoazepanes and 1-deoxy-homonojirimycin analogues: synthesis and glycosidase inhibition study

S. D. Markad, N. S. Karanjule, T. Sharma, S. G. Sabharwal and D. D. Dhavale, Org. Biomol. Chem., 2006, 4, 3675 DOI: 10.1039/B609000A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements