203783-02-2

Upstream product

• 203783-01-1 (3S,8R,8aR)-8-Hydroxy-8a-methyl-3-phenyl-2,3,8,8a-tetrahydro-oxazolo[3,2-a]pyridin-5-one 

Downstream Products

• 203783-03-3 (3aR,5S,7aR,8R,8aR)-8-Hydroxy-2,2,7a-trimethyl-5-phenyl-hexahydro-1,3,7-trioxa-4a-aza-s-indacen-4-one 
• 135395-45-8 1,5,6-trideoxy-1,5-imino-L-mannitol 

Relevant academic research and scientific papers

Asymmetric routes to azasugars from chiral bicyclic lactams. Synthesis of 1,4-dideoxy-1,4-imino-d-lyxitol; L-Deoxymannojirimycin; rhammo-1- Deoxynojirimycin and 1-deoxy-6-epicastanospermine

Summary: By employing the appropriate chiral bicyclic lactams, the asymmetric total synthesis of four enantiopure azasugars mentioned in the title were successfully achieved. A series of diastereoselective oxidations (OsO4/NMO) followed by diastereoselective reductions (BH3, 9-BBN) gave good yields of the trisubstituted (16) and tetrasubstituted (2,3,4) pyrrolidine and piperidines respectively.