74055-39-3

Upstream product

• 74063-01-7 8-hydroxymethyl-des-AB-cholest-8-ene 
• 74055-37-1 (1S,5R)-3-hydroxymethyl-4-methylcyclohex-3-ene-1,5-diol bis(t-butyldimethylsilyl) ether 
• 75211-99-3 8-p-tolylsulphonylmethyl-des-AB-cholest-8-ene 
• 3752-57-6 8-hydroxymethyl-des-AB-cholest-8-ene p-nitrobenzoate 
• 74055-35-9 methyl (3S,5R)-3,5-dihydroxy-2-methylcyclohex-1-ene-1-carboxylate 
• 74064-29-2 (3R,3aR,7aR)-7-Chloromethyl-3-((R)-1,5-dimethyl-hexyl)-3a-methyl-2,3,3a,4,5,7a-hexahydro-1H-indene 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 74064-30-5 (3S,5R)-3,5-Bis[(tert-butyldimethylsilyl)oxy]-2-methylcyclohex-1-en-1-carboxaldehyde 
• 74055-36-0 methyl (3S,5R)-3,5-bis-t-bytyldimethylsilyloxy-2-methylcyclohex-1-enecarboxylate 
• 31915-47-6 (1S,5S)-2-Methyl-6-oxa-bicyclo[3.2.1]oct-2-en-7-one 
• 55365-49-6 5α,6α-epoxy-6-methylcyclohexane-1β,3β-carbolactone 
• 74055-38-2 Benzoic acid 1-[(3S,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-cyclohex-1-enyl]-2-[(1R,3aR,7aR)-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl]-2-(toluene-4-sulfonyl)-ethyl ester 

Downstream Products

• 108887-35-0 1α,3β-bis(tert-butyldimethylsilyloxy)-9,10-secocholesta-5,7,10(19)-triene 
• 41294-56-8 1α-hydroxyvitamin D3 

Relevant academic research and scientific papers

Calciferol and its Relatives. Part 27. A Synthesis of 1α-Hydroxyvitamin D3 by way of 1α-Hydroxytachysterol3

A new synthesis of 1α-hydroxyvitamin D3 is described.The bis-t-butyldimethylsilyl ether (17) of (3S,5R)-3,5-dihydroxy-2-methylcyclohex-1-enecarbaldehyde and 8-p-tolylsulphonylmethyl-des-AB-cholest-8-ene (4) were combined to give mixed benzoyloxysulphones which, on reductive elimination with sodium amalgam, gave the corresponding bis-ether of 1α-hydroxytachysterol3.This was isomerised photochemically to the bis-ether of 1α-hydroxyprecalciferol3, and then thermally to give the bis-ether of 1α-hydroxyvitamin D3.Removal of protecting groups gave 1α-hydroxyvitamin D3 (21) in 62percent yield from the sulphone (4), or 12.8percent overall from cholesterol.