191600-89-2

Upstream product

• 100-44-7 benzyl chloride 
• 72081-17-5 hydroxymethyl-2 dihydro-3,4 2H-pyranne 
• 89429-82-3 6-benzyloxymethyl-3,4-dihydro-2H-pyran 
• 110-87-2 3,4-dihydro-2H-pyran 
• 191600-87-0 (3S,8aS)-8a-Benzyloxymethyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-one 
• 191600-86-9 6-Benzyloxy-5-oxo-hexanoic acid 
• 191600-88-1 (3S,8aS)-8a-Benzyloxymethyl-3-phenyl-2,3,8,8a-tetrahydro-oxazolo[3,2-a]pyridin-5-one 

Downstream Products

• 191600-90-5 (3S,6R,7R,8R,8aR)-8a-Benzyloxymethyl-6,7,8-trihydroxy-3-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-one 
• 191600-91-6 (3aR,5S,7aR,8R,8aR)-7a-Benzyloxymethyl-8-hydroxy-2,2-dimethyl-5-phenyl-hexahydro-1,3,7-trioxa-4a-aza-s-indacen-4-one 
• 191600-92-7 (3aS,6S,7S,7aR)-6-Benzyloxymethyl-5-((S)-2-hydroxy-1-phenyl-ethyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridin-7-ol 

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.

Asymmetric synthesis of L-deoxymannojirimycin

Starting from dihydropyran 1, the chiral lactam 4 was rapidly obtained. Following unsaturation, highly diastereoselective allylic oxidation and dihydroxylation furnished lactam 7 from which the azasugar, L-deoxymannojirimycin, could be prepared.