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
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
April 2016
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), .
(doi:10.1055/s-0035-1561323).
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.
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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
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Date deposited: 31 Jul 2019 16:30
Last modified: 17 Mar 2024 12:31
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Contributors
Author:
Fabien Stauffert
Author:
Mathieu L. Lepage
Author:
Damien Hazelard
Author:
Anne Bodlenner
Author:
Philippe Compain
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