386743-52-8

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 308123-37-7 (1R,3aR,4S,7aR)-1-((1S,2S)-2-Hydroxymethyl-1,5-dimethyl-5-triethylsilanyloxy-hexyl)-7a-methyl-octahydro-inden-4-ol 
• 93489-60-2 <1R-<1β(R*),3aα,4β,7aβ>>-octahydro-4-hydroxy-β,7a-dimethyl-1H-indene-1-propanenitrile 
• 145223-32-1 2-[(S)-1-((1R,3aR,4S,7aR)-4-Hydroxy-7a-methyl-octahydro-inden-1-yl)-ethyl]-5-methyl-5-triethylsilanyloxy-hexanenitrile 
• 87417-12-7 (3-bromo-1,1-dimethylpropoxy)triethylsilane 

Downstream Products

• 393184-85-5 Toluene-4-sulfonic acid (S)-2-((S)-1-{(1R,3aS,7aR)-4-[2-[(S)-5-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-ethyl)-5-methyl-5-triethylsilanyloxy-hexyl ester 
• 393184-88-8 Toluene-4-sulfonic acid (S)-5-methyl-2-[(S)-1-((1R,3aR,7aR)-7a-methyl-4-oxo-octahydro-inden-1-yl)-ethyl]-5-triethylsilanyloxy-hexyl ester 

Relevant academic research and scientific papers

Rapid access to a series of calcitriol analogues with restricted side chain conformation

The synthesis of a series of calcitriol analogues with restricted side chain conformation is described. C-22 modified calcitriol analogues have been prepared from a common intermediate, in which the labile triene system is already present.

Stereoselective synthesis of (22R)- and (22S)-22-methyl-1α,25-dihydroxy-vitamin D3

An efficient, straightforward method for construction of the side chain of (22R)- and (22S)-22-alkyl-1α,25-dihydroxyvitamin D3 is described. The title compounds were synthesized by Lythgoe's procedure.

A key intermediate for the convenient synthesis of series of vitamin D3 analogues with modified side chains

Tosylate 1, which features the vitamin D triene unit, was stereoselectively synthesized from commercially available starting materials. This key intermediate undergoes a very efficient one-pot, two-step reaction with tetrabutyl ammonium fluoride to afford vitamin D analogue 2, which bears a cyclic side chain. Reaction of 1 with lithium aluminium hydride and removal of the silyl protecting groups affords the 22-methylated vitamin D analogue 3.