161793-07-3

Basic information

• Product Name: (2S,3S)-2-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-6-methyl-6-triethylsilanyloxy-heptan-3-ol
• Synonyms: (2S,3S)-2-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-6-methyl-6-triethylsilanyloxy-heptan-3-ol
• CAS NO: 161793-07-3
• Molecular Weight: 775.432
• Mol File: 161793-07-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2S,3S)-2-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-6-methyl-6-triethylsilanyloxy-heptan-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S)-2-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-6-methyl-6-triethylsilanyloxy-heptan-3-ol(161793-07-3)
• EPA Substance Registry System: (2S,3S)-2-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-6-methyl-6-triethylsilanyloxy-heptan-3-ol(161793-07-3)

Safety Data

• Hazardous Substances Data: 161793-07-3(Hazardous Substances Data)

Upstream product

• 112924-91-1 (5Z,7E)-(1S,3R,20S)-1,3-bis<(tert-butyldimethylsilyl)oxy>-9,10-seco-22,23-dinor-5,7,10(19)-cholatrien-24-al 
• 87417-12-7 (3-bromo-1,1-dimethylpropoxy)triethylsilane 

Downstream Products

• 161793-09-5 (1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-1-((1S,2S)-2-iodo-1,5-dimethyl-5-triethylsilanyloxy-hexyl)-7a-methyl-octahydro-indene 
• 161793-10-8 (1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-1-((1S,2R)-2-iodo-1,5-dimethyl-5-triethylsilanyloxy-hexyl)-7a-methyl-octahydro-indene 
• 167948-89-2 (1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-1-((E)-1,5-dimethyl-5-triethylsilanyloxy-hex-1-enyl)-7a-methyl-octahydro-indene 
• 161793-08-4 Toluene-4-sulfonic acid (S)-1-((S)-1-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-ethyl)-4-methyl-4-triethylsilanyloxy-pentyl ester 

Relevant articles and documents

Synthesis and biological activity of 22-iodo- and (E)-20(22)-dehydro analogues of 1α,25-dihydroxyvitamin D3

Construction of 25-hydroxy-steroidal side chain substituted with iodine at C-22 was elaborated on a model PTAD-protected steroidal 5,7-diene and applied to a synthesis of (22R)- and (22S)-22-iodo-1α,25-dihydroxyvitamin D3. Configuration at C-22 in the iodinated vitamins, obtained by nucleophilic substitution of the corresponding 22S-tosylates with sodium iodide, was determined by comparison of their iodine-displacement processes and cyclizations leading to isomeric five-membered (22,25)-epoxy-1α-hydroxyvitamin D3 compounds. Also, 20(22)-dehydrosteroids have been obtained and their structures established by 1H NMR spectroscopy. When compared to the natural hormone, (E)-20(22)-dehydro-1α,25-dihydroxyvitamin D3 was found 4 times less potent in binding to the porcine intestinal vitamin D receptor (VDR) and 2 times less effective in differentiation of HL-60 cells. 22-Iodinated vitamin D analogues showed somewhat lower in vitro activity, whereas (22,25)-epoxy analogues were inactive. Interestingly, it was established that (22S)-22-iodo-1α,25-dihydroxyvitamin D3 was 3 times more potent than its (22R)-isomer in binding to VDR and four times more effective in HL-60 cell differentiation assay. The restricted mobility of the side chain of both 22-iodinated vitamin D compounds was analyzed by a systematic conformational search indicating different spatial regions occupied by their 25-oxygen atoms. Preliminary data on the in vivo calcemic activity of the synthesized vitamin D analogues indicate that (E)-20(22)-dehydro-1α,25-dihydroxyvitamin D3 and 22-iodo-1α,25-dihydroxyvitamin D3 isomers were ca. ten times less potent than the natural hormone 1α,25-(OH)2D3 both in intestinal calcium transport and bone calcium mobilization. Copyright (C) 1999 Elsevier Science Ltd.