The University of Southampton
University of Southampton Institutional Repository

A convenient, gram-scale synthesis of 1-deoxymannojirimycin

A convenient, gram-scale synthesis of 1-deoxymannojirimycin
A convenient, gram-scale synthesis of 1-deoxymannojirimycin

A novel gram-scale synthesis of 1-deoxymannojirimycin from tetra-O-benzyl-d-glucopyranose in 9 steps and 28% overall yield with a limited number of purification steps is reported. The synthetic strategy is based on the regioselective deprotection and subsequent inversion of configuration of the OH group at C-2 in tetra-O-benzyl-d-glucono-δ-lactam, also an advanced intermediate toward the synthesis of 1-deoxynojirimycin derivatives.

chiral pool, glycosidase inhibitors, iminosugars, multi-step synthesis, natural products
0039-7881
1177-1180
Stauffert, Fabien
77e7c9e7-5828-4683-97e0-41381cc06842
Lepage, Mathieu L.
b12fc6ec-e309-4d91-9fd5-adc7fdd79b85
Pichon, Maëva M.
84bb0e1a-a659-4e77-9dbd-6b61d2fa2a31
Hazelard, Damien
ce714859-0244-468d-bcda-40eb687e8a90
Bodlenner, Anne
a97ef344-4e55-47b5-8f7d-90799d615519
Compain, Philippe
adb871dd-570e-4b25-96f2-cd0462627f52
Stauffert, Fabien
77e7c9e7-5828-4683-97e0-41381cc06842
Lepage, Mathieu L.
b12fc6ec-e309-4d91-9fd5-adc7fdd79b85
Pichon, Maëva M.
84bb0e1a-a659-4e77-9dbd-6b61d2fa2a31
Hazelard, Damien
ce714859-0244-468d-bcda-40eb687e8a90
Bodlenner, Anne
a97ef344-4e55-47b5-8f7d-90799d615519
Compain, Philippe
adb871dd-570e-4b25-96f2-cd0462627f52

Stauffert, Fabien, Lepage, Mathieu L., Pichon, Maëva M., Hazelard, Damien, Bodlenner, Anne and Compain, Philippe (2016) A convenient, gram-scale synthesis of 1-deoxymannojirimycin. Synthesis (Germany), 48 (8), 1177-1180. (doi:10.1055/s-0035-1561323).

Record type: Article

Abstract

A novel gram-scale synthesis of 1-deoxymannojirimycin from tetra-O-benzyl-d-glucopyranose in 9 steps and 28% overall yield with a limited number of purification steps is reported. The synthetic strategy is based on the regioselective deprotection and subsequent inversion of configuration of the OH group at C-2 in tetra-O-benzyl-d-glucono-δ-lactam, also an advanced intermediate toward the synthesis of 1-deoxynojirimycin derivatives.

This record has no associated files available for download.

More information

Accepted/In Press date: 15 December 2015
e-pub ahead of print date: 20 January 2016
Published date: April 2016
Keywords: chiral pool, glycosidase inhibitors, iminosugars, multi-step synthesis, natural products

Identifiers

Local EPrints ID: 432873
URI: http://eprints.soton.ac.uk/id/eprint/432873
ISSN: 0039-7881
PURE UUID: 04cd1d36-4846-4ffa-a2f6-52b1061f93a0

Catalogue record

Date deposited: 31 Jul 2019 16:30
Last modified: 17 Mar 2024 12:31

Export record

Altmetrics

Contributors

Author: Fabien Stauffert
Author: Mathieu L. Lepage
Author: Damien Hazelard
Author: Anne Bodlenner
Author: Philippe Compain

Download statistics

Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.

View more statistics

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton: eprints@soton.ac.uk

ePrints Soton supports OAI 2.0 with a base URL of http://eprints.soton.ac.uk/cgi/oai2

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.

×