Expeditious synthesis of a common intermediate of L-1-deoxyallonojirimycin and L-1-deoxymannojirimycin.
The expeditious synthesis of a common intermediate of L-1-deoxyallonojirimycin (L-allo-DNJ) and L-1-deoxymannojirimycin (L-manno-DNJ) is reported. This intermediate is obtained in highly diastereo- and enantioselectivity with 38.4% overall yield in six steps involving the unprecedented ring-closing metathesis of a tert-butylsulfinyl allylamine as the key step.
Ferreira
Franck
F
UPMC Univ Paris 06 and CNRS, UMR 7611, Laboratoire de Chimie Organique, Institut de Chimie Moléculaire (FR 2769), case 183, 4 place Jussieu, F-75005 Paris, France. franck.ferreira@upmc.fr
Botuha
Candice
C
Chemla
Fabrice
F
Pérez-Luna
Alejandro
A
D017485:1-Deoxynojirimycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000499:Allylamine / Q000031:analogs & derivatives* / Q000737:chemistry*; D003500:Cyclization; D008968:Molecular Conformation; D013237:Stereoisomerism
C551691:L-1-deoxyallonojirimycin; C551690:L-1-deoxymannojirimycin; D017485:1-Deoxynojirimycin; D000499:Allylamine