17488-99-2

Upstream product

• 29569-71-9 (S)-5-Hydroxy-2-methyl-cyclohex-1-enecarbaldehyde 
• 75212-00-9 (S)-5-benzoyloxy-2-methylcyclohex-1-ene-1-carbaldehyde 
• 75212-01-0 3β,6-dibenzoyloxy-7-p-tolylsulphonyl-9,10-seco-cholesta-5(10),8-diene 
• 434-16-2 7-dehydrocholesterol 
• 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 
• 3752-57-6 8-hydroxymethyl-des-AB-cholest-8-ene p-nitrobenzoate 
• 75211-99-3 8-p-tolylsulphonylmethyl-des-AB-cholest-8-ene 
• 74063-01-7 8-hydroxymethyl-des-AB-cholest-8-ene 

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.