239136-90-4

Upstream product

• 16310-55-7 2-((benzyloxy)methyl)-2,3-dihydrofuran 
• 3587-60-8 Benzyloxymethyl chloride 
• 107757-75-5 2-benzyloxymethyl-4,5-dihydrofuran 
• 20989-17-7 (2S)-2-phenylglycinol 
• 176095-95-7 (3aR,3bR,6S,7aS)-3b-Benzyloxymethyl-2,2-dimethyl-6-phenyl-tetrahydro-1,3,4-trioxa-6a-aza-cyclopenta[a]pentalen-7-one 
• 176095-96-8 (3S,6S,7R,7aR)-7a-Benzyloxymethyl-6,7-dihydroxy-3-phenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one 
• 176298-37-6 (3S,7aS)-7a-Benzyloxymethyl-3-phenyl-2,3-dihydro-7aH-pyrrolo[2,1-b]oxazol-5-one 
• 176298-36-5 (3S,7aS)-7a-Benzyloxymethyl-3-phenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one 
• 167645-47-8 5-(benzyloxy)-4-oxopentanoic acid 

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.