A Convenient, Gram-Scale Synthesis of 1-Deoxymannojirimycin

A Convenient, Gram-Scale Synthesis of 1-Deoxymannojirimycin

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 configuratio...

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Veröffentlicht in:Synthesis (Stuttgart) 2016-01, Vol.48 (8), p.1177-1180
Hauptverfasser: Stauffert, Fabien, Lepage, Mathieu L., Pichon, Maëva M., Hazelard, Damien, Bodlenner, Anne, Compain, Philippe
Format: Artikel
Sprache:eng
Schlagworte:
Chemical Sciences
Organic chemistry
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Zusammenfassung: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.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0035-1561323