386761-64-4

Upstream product

• 386761-62-2 (2R,3R,6S)-6-azido-3-(benzyloxy)-non-8-ene-1,2-diol 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 124-63-0 methanesulfonyl chloride 
• 386761-63-3 (2R,3R,6S)-6-azido-3-(benzyloxy)-1-[(tert-butyldiphenylsilyl)oxy]non-8-ene-2-ol 

Downstream Products

• 386761-66-6 (2S,3R,6S)-6-allyl-3-(benzyloxy)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}piperidine 
• 386761-67-7 (2S,3R,6S)-6-allyl-3-(benzyloxy)-1-[(benzyloxy)carbonyl]-2-{[(tert-butyldiphenylsilyl)oxy]methyl}piperidine 
• 386761-69-9 12-((2R,5R,6S)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}piperidin-2-yl)-5-hydroxydodecan-3-one 
• 386761-68-8 12-((2S,5R,6S)-5-(benzyloxy)-1-[(benzyloxy)carbonyl]-6-{[(tert-butyldiphenylsilyl)oxy]methyl}piperidin-2-yl)dodec-10-en-3-one 
• 386761-65-5 (4S,7R,8R)-7-(benzyloxy)-9-[(tert-butyldiphenylsilyl)oxy]-8-[(methylsulfonyl)oxy]non-1-en-4-amine 

Relevant academic research and scientific papers

Enantioselective allyltitanations and metathesis reactions. Application to the synthesis of piperidine alkaloids (+)-sedamine and (-)-prosophylline

An enantioselective synthesis of the piperidine alkaloids (+)-sedamine and (-)-prosophylline is reported. The synthesis of (+)-sedamine has been achieved in 12 steps with an overall yield of 20% from benzaldehyde, and (-)-prosophylline was obtained in 15 steps with an overall yield of 9.2%, starting from D-glyceraldehyde acetonide 14. The key steps are enantioselective allyltitanation reactions and ring-closing or cross-metathesis reactions.

Enantioselective allyltitanation and cross-metathesis. Synthesis of (-)-prosophylline

An enantioselective synthesis of (-)-prosophylline has been accomplished in 15 steps from protected D-glyceraldehyde, with an overall yield of 9.2%, by using two enantioselective allyltitanations and a cross-metathesis reaction as the key-steps.