Synthesis of 1-deoxy-D-galactohomonojirimycin via enantiomerically pure allenylstannanes.
1-Deoxy-D-galactohomonojirimycin was synthesized in seven steps from optically pure allenylstannane 4 and L-lactate-derived aldehyde 5 in 48% overall yield. The key step was the Lewis acid catalyzed reaction of 4 and 5 to give the syn-amino alcohol in excellent yield and very high diastereoselectivity.
Achmatowicz
Michal
M
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
Hegedus
Louis S
LS
D017485:1-Deoxynojirimycin / Q000031:analogs & derivatives; D000447:Aldehydes / Q000737:chemistry; D000470:Alkaloids / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D005690:Galactose / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D019344:Lactic Acid / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010880:Piperidines / Q000032:analysis / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014001:Tin / Q000737:chemistry*
C486051:1-deoxy-D-galactohomonojirimycin; D000447:Aldehydes; D000470:Alkaloids; D007202:Indicators and Reagents; D009942:Organometallic Compounds; D010880:Piperidines; D017485:1-Deoxynojirimycin; D019344:Lactic Acid; D014001:Tin; D005690:Galactose