386766-84-3

Upstream product

• 326599-39-7 methyl (1R,3S,5R)-3-tert-(butyldiphenylsilyloxy)-5-tosyloxycyclohexanecarboxylate 
• 326599-41-1 [(1S,3R,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-bicyclo[3.1.0]hex-1-yl]-methanol 
• 326599-42-2 (2R,3aS,4aS)-2-(tert-butyldiphenylsilyloxy)bicyclo[3.1.0]hexane-3a-carbaldehyde 
• 326599-02-4 methyl (1R,3S,5R)-3-hydroxy-5-tosyloxycyclohexanecarboxylate 
• 326598-94-1 (1S,3S,5R)-3-acetoxy-5-hydroxy-1-(methoxycarbonyl)cyclohexane 
• 326599-40-0 methyl(2R,3aS,4aS)-2-(tert-butyldiphenylsilyloxy)bicyclo[3.1.0]-hexane-3a-carboxylate 
• 326599-01-3 Methyl (1R,3S,5R)-3-acetoxy-5-tosyloxy-cyclohexanecarboxylate 

Relevant academic research and scientific papers

A practical synthesis of 14-epi-19-nor-1α,25-dihydroxyvitamin D3 analogues and their A-ring epimers

A practical synthesis of (2S,3aS,4aS)-2-tert-butyldimethylsilyloxybicyclo[3.1.0]hexane-3a-carbaldehyde (14a) and diastereoisomers, starting from all-cis methyl 3,5-dihydroxy-1cyclohexanecarboxylate (24) is described. Coupling with appropriate cis-hydrindanes produces the title compounds. TX 522, a member of this series, is currently in phase II clinical studies for the treatment of psoriasis. The key step involves the coupling of 14 and 16 with the respective cis-hydrindanes 9 and 7.