75211-99-3

Upstream product

• 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 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 75443-92-4 (1R,3aR,7aR)-1-((R)-1,5-Dimethyl-hexyl)-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-indene-4-carboxylic acid methyl ester 
• 74063-01-7 8-hydroxymethyl-des-AB-cholest-8-ene 
• 3752-57-6 8-hydroxymethyl-des-AB-cholest-8-ene p-nitrobenzoate 
• 62151-32-0 (2R,3R)-2-methyl-3-[(1R)-1,5-dimethylhexyl]cyclopentanone 
• 87530-51-6 (2R,3R)-3-((R)-1,5-Dimethyl-hexyl)-2-methyl-2-(3-oxo-butyl)-cyclopentanone 
• 87530-56-1 (1R,3aS,4R,5R,7aR)-5-Benzoyloxy-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-octahydro-indene-4-carboxylic acid methyl ester 
• 87530-57-2 (1R,3aS,4R,5R,7aR)-1-((R)-1,5-Dimethyl-hexyl)-7a-methyl-5-(toluene-4-sulfonyloxy)-octahydro-indene-4-carboxylic acid methyl ester 
• 87530-53-8 (1R,7aR)-1-((R)-1,5-Dimethyl-hexyl)-7a-methyl-5-oxo-2,3,5,6,7,7a-hexahydro-1H-indene-4-carboxylic acid 
• 87530-55-0 (1R,3aS,4R,7aR)-1-((R)-1,5-Dimethyl-hexyl)-7a-methyl-5-oxo-octahydro-indene-4-carboxylic acid methyl ester 
• 87530-54-9 (1R,3aS,4R,7aR)-1-((R)-1,5-Dimethyl-hexyl)-7a-methyl-5-oxo-octahydro-indene-4-carboxylic acid 
• 87530-52-7 (1R,7aR)-1-[(1R)-1,5-dimethylhexyl]-1,2,3,6,7,7a-hexahydro-7a-methyl-5H-inden-5-one 
• 87680-13-5 (1R,3aS,4R,5R,7aR)-1-((R)-1,5-Dimethyl-hexyl)-5-hydroxy-7a-methyl-octahydro-indene-4-carboxylic acid methyl ester 

Downstream Products

• 74055-41-7 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)-ethanone 
• 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 
• 41294-56-8 1α-hydroxyvitamin D3 
• 1173-13-3 previtamin D₃ 
• 17592-07-3 tachysterol₃ 
• 17488-99-2 tachysterol₃ 4-methyl-3,5-dinitrobenzoate 
• 108887-35-0 1α,3β-bis(tert-butyldimethylsilyloxy)-9,10-secocholesta-5,7,10(19)-triene 
• 74055-39-3 (3R,3aR,7aR)-7-{(E)-2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-cyclohex-1-enyl]-vinyl}-3-((R)-1,5-dimethyl-hexyl)-3a-methyl-2,3,3a,4,5,7a-hexahydro-1H-indene 
• 74064-31-6 Phosphoric acid (E)-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)-vinyl ester diethyl ester 
• 75212-01-0 3β,6-dibenzoyloxy-7-p-tolylsulphonyl-9,10-seco-cholesta-5(10),8-diene 

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.