142913-83-5

Upstream product

• 100-46-9 benzylamine 
• 13039-93-5 2,2:4,5-di-O-isopropylidene-D-arabinose 
• 23568-31-2 2,3:4,5-di-O-isopropylidene-L-arabinose 

Downstream Products

• 146467-03-0 cis-1-benzyl-3S-benzyloxy-4R-[1'R,2'S,3'R,4'-di-O-isopropylidene]butyl-azetidin-2-one 
• 152532-91-7 5-N-benzylamino-6,7;8,9-di-O-isopropylidene-2,3,5-trideoxy-D-glycero-D-talo-non-2-enono-1,4-lactone 
• 142913-84-6 N-benzyl-(6S,1'R,2'S,3'R)-6-(1',2':3',4'-di-O-isopropylidene-1',2',3',4'-tetrahydroxy-1'-butyl)-2,3-didehydropiperidine-4-one 
• 143004-83-5 N-benzyl-(6R,1'R,2'S,3'R)-6-(1',2':3',4'-di-O-isopropylidene-1',2',3',4'-tetrahydroxy-1'-butyl)-2,3-didehydropiperidine-4-one 
• 152532-96-2 5-N-benzylamino-6,7;8,9-di-O-isopropylidene-2,3,5-trideoxy-L-glycero-L-talo-non-2-enono-1,4-lactone 
• 160962-76-5 N-benzyl-(6S,1'S,2'R,3'S)-6-(1',2':3',4'-di-O-isopropylidene-1',2',3',4'-tetrahydroxy-1'-butyl)-2,3-didehydropiperidine-4-one 
• 160962-75-4 N-benzyl-(6R,1'S,2'R,3'S)-6-(1',2':3',4'-di-O-isopropylidene-1',2',3',4'-tetrahydroxy-1'-butyl)-2,3-didehydropiperidine-4-one 
• 142913-85-7 N-benzyl-(2R,4S,1'S,2'R,3'S)-2-(1',2':3',4'-di-O-isopropylidene-1',2',3',4'-tetrahydroxy-1'-butyl)-4-hydroxypiperidine 
• 142913-86-8 N-benzyl-(2R,4S,1'S,2'R,3'S)-2-(1',2'-O-isopropylidene-1',2',3',4'-tetrahydroxy-1'-butyl)-4-hydroxypiperidine 
• 142913-87-9 (4R,5S)-5-((2R,4S)-1-Benzyl-4-hydroxy-piperidin-2-yl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde 

Relevant academic research and scientific papers

Efficient total syntheses of (1R, 2R, 3R, 9R, 9aR)-1,2,3,9-tetrahydroxyquinolizidine and its enantiomer

Concise syntheses of two enantiomeric tetrahydroxyquinolizidines, 10 and ent-10 have been achieved from D-arabinose and L-arabinose, respectively. Highly diastereoselective homologation of imine 5 (or ent-5) using 2-(trimethylsiloxy)furan provided the nine-carbon butenolide 6 (or ent-6) which was elaborated into the quinolizidine 10 (or ent-10) via a clean sequence involving, as key operations, DBU-promoted γ-lactone to δ-lactam ring expansion (e.g. 7 to 8) and cyclodehydration of a fully-deprotected hydroxypiperidine employing Ph3, CCl4, Et3N (e.g. 9 to 10). The procedure comprises five steps from 5 or ent-5 and provides the title quinolizidine 10 or its enantiomer ent-10 in 36-37% overall yields.

Versatile β-Lactam Synthons: Enantiospecific Synthesis of (-)-Polyoxamic Acid

An optically pure cis-α-hydroxy β-lactam of predictable absolute configuration prepared from readily available D-mannitol has been utilized for the synthesis of the non-natural enantiomer of polyoxamic acid through a series of stereospecific reactions.

Cycloaddition Reactions of Carbohydrate Derivatives. Part III. A New Route to Swainsonine Analogs.

Swainsonine analogs 10 and 12 have been synthesized from D- and L-arabinose, respectively, using cyclocondensation of azomethines with Danisthefsky's diene followed by stereoselective carbonyl and double bond reduction of the resulting pyridones, chain sh