1379672-05-5

Upstream product

• 1379671-99-4 1-((4R,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-nitrobutan-1-one 
• 1379672-00-0 1-((4R,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-nitrobutan-1-one 
• 1379672-02-2 (3aR,7S,8S,8aS)-8-hydroxy-2,2-dimethyl-7-nitrotetrahydro-3aH-cyclohepta[d][1,3]dioxol-4(5H)-one 
• 1379672-04-4 tert-butyl ((3aS,4S,5S,8aR)-4-hydroxy-2,2-dimethyl-8-oxohexahydro-3aH-cyclohepta[d][1,3]dioxol-5-yl)carbamate 
• 1379672-01-1 C₁₀H₁₅NO₆ 
• 1379671-98-3 C₁₅H₂₈O₄Si 

Relevant academic research and scientific papers

Total synthesis of ent-calystegine B4 via nitro-Michael/aldol reaction

Optically active ent-calystegine B4 was prepared in 13 steps from commercially available chiral l-dimethyl tartrate. The synthesis was achieved by the Michael addition and the aldol reaction of nitromethane to form cycloheptanone in a stereoselective manner. Reduction of the nitro group in the presence of Boc2O accomplished an efficient conversion to amino cycloheptanone, which readily afforded the desired ent-calystegine B4.