96685-53-9

Usage

InChI:InChI=1/C15H28O2Si/c1-12-7-8-14(11-13(12)9-10-16)17-18(5,6)15(2,3)4/h9,14,16H,1,7-8,10-11H2,2-6H3/b13-9-/t14-/m0/s1

Upstream product

• 84927-67-3 3β-O-(tert-butyldimethylsilyl)-7,8-dihydroxy-7,8-dihydrovitamin D3 
• 84927-66-2 7,8-dihydroxy-7,8-dihydrovitamin D₃ 
• 150255-34-8 (4-Bromo-1-prop-2-ynyl-pent-4-enyloxy)-tert-butyl-dimethyl-silane 
• 156137-75-6 7-Bromo-oct-7-en-1-yn-4-ol 
• 50-14-6 vitamin D₂ 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 67337-15-9 <(1Z),(5S)>-2-<5-hydroxy-2-methylcyclohexylidene>-ethanol 
• 935-79-5 cis-1,2,3,6-tetrahydrophthalic anhydride 
• 104846-62-0 3(S)-tert-butyldimethylsilyloxy-9,10-secoergosta-5,7(E),10⁽¹⁹⁾,22(E)-tetraene 
• 1014717-75-9 (S,Z)-tert-butyl(2-(5-((tert-butyldimethylsilyl)oxy)-2-methylenecyclohexylidene)ethoxy)dimethylsilane 

Downstream Products

• 138313-18-5 <(1Z),(5S)>-2-<5-(t-butyldimethylsilyl)oxy-2-methylenecyclohexylidene>-1-chloroethane 
• 96688-64-1 (2Z)-<(5S)-5-(tert-butyldimethylsilyloxy)-2-methylene-cyclohexylidene>acetaldehyde 
• 245115-89-3 (Z,S)-2-[2-[5-(tert-Butyldimethylsilyloxy)-2-methylenecyclohexylidene]ethylsulfanyl]benzothiazole 
• 869101-42-8 {(S)-3-[2-Bromo-eth-(Z)-ylidene]-4-methylene-cyclohexyloxy}-tert-butyl-dimethyl-silane 
• 50-14-6 Calciferol 
• 247900-07-8 (7Z)-Vitamin D₂ 
• 100858-27-3 (S)-(Z)-{2-[5-(tert-butyldimethylsiloxy)-2-methylenecyclohexylidene]ethyl}diphenylphosphine oxide 
• 84927-61-7 23-oxa-25-hydroxyvitamin D₃ 
• 84927-72-0 23-oxa-25,26-dehydrovitamin D₃ 
• 84927-73-1 tert-Butyl-dimethyl-{(S)-4-methylene-3-[2-[(1R,3aS,7aR)-7a-methyl-1-[(S)-1-methyl-2-(2-methyl-allyloxy)-ethyl]-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-cyclohexyloxy}-silane 
• 651734-12-2 20S-Hydroxyvitamin D₃ 
• 199798-84-0 1-alpha-fluoro-25-hydroxy-16,23E-diene-26,27-bishomo-20-epi-cholecalciferol 
• 926315-15-3 benzoic acid 2-[(3S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-3-fluoro-2-methylene-cyclohex-(Z)-ylidene]-ethyl ester 
• 926315-12-0 benzoic acid (2R,3S,7S)-7-((t-butyldimethyl)silanyloxy)-4-methylene-1-oxa-spiro[2.5]oct-2-yl methyl ester 

Relevant academic research and scientific papers

Total synthesis of biologically active 20S-hydroxyvitamin D3

A total synthetic strategy of 20S-hydroxyVitamin D3 [20S-(OH)D3] involving modified synthesis of key intermediates 7 and 12, Grignard reaction to stereoselectively generate 20S-OH and Wittig-Horner coupling to establish D3 framework, was completed in 16 steps with an overall yield of 0.4%. The synthetic 20S-(OH)D3 activated Vitamin D receptor (VDR) and initiated the expression of downstream genes. In addition, 20S-(OH)D3 showed similar inhibitory potency as calcitriol [1,25(OH)2D3] on proliferation of melanoma cells.

Asymmetric Synthesis of Vitamin D3 Analogues: Organocatalytic Desymmetrization Approach toward the A-Ring Precursor of Calcifediol

A novel asymmetric synthesis has been developed for the construction of the A-ring of a chiral precursor to calcifediol. The highlights of this synthesis include (i) the introduction of the stereochemistry at the C5-position of the A-ring through the orga

Furan approach to vitamin D analogues. Synthesis of the A-ring of calcitriol and 1α-hydroxy-3-deoxyvitamin D3

The A-rings of calcitriol (1α,25-dihydroxyvitamin D3) and 1α-hydroxy-3-deoxyvitamin D3 were synthesized using the furan approach. The critical steps in the synthesis of the A-ring of calcitriol involved an asymmetric carbonyl-ene reaction of 3-methylene-2,3-dihydrofuran with 3-(tert-butyldimethylsiloxy)propanal, a diastereoselective Friedel-Crafts hydroxyalkylation, an oxidation of the 2,3-disubstituted furan to give a γ-hydroxybutenolide, and a Peterson olefination. The A-ring (Z)-dienol of calcitriol was synthesized in 12 steps from 3-(tert-butyldimethylsiloxy)propanal in 17% yield.

NOVEL METHOD

There is provided a method of prevention of adhesions, eg surgical adhesions, which comprises using a vitamin D compound.

SYNTHESIS OF 1α-FLUORO-25-HYDROXY-16-23E-DIENE-26,27-BISHOMO-20-EPI-CHOLECALCIFEROL

The invention provides a method of producing 20-methyl vitamin D3 compounds of formula (I). The method includes hydroxylation, carbonyl reduction, fluoride substitution, epoxide deoxygenation, and Wittig-type couplings.

NOVEL METHOD

The invention provides for the use of Vitamin D compounds such as 1-alpha-fluoro-25- hydroxy-16,23E-diene-26,27-bishomo-20-epi-cholecalciferol, in the prevention or treatment of prostate cancer.

SYNTHESIS OF 1α-FLUORO-25-HYDROXY-16-23E-DIENE-26,27-BISHOMO-20-EPI-CHOLECALCIFEROL

The invention provides a method of producing 20-methyl vitamin D3 compounds of formula (I). The method includes allylic and olefin oxidation, decarbonylation, carbonyl reduction, fluoride substitution, epoxide deoxygenation, and Wittig-type couplings.

Preparation of an A-ring building block for the total synthesis of 1α,25-dihydroxy vitamin D3 and structurally related congeners: Lipase-catalyzed stereoselective esterification of a suitable epoxyalcohol

An useful A-ring building block for the total synthesis of vitamin D3 congeners, compound 7, has been prepared starting from vitamin D2 by a chemo-enzymatic approach that relies on lipase-catalyzed acylation in an organic solvent for the stereoselective step. Copyright (C) 2000 Elsevier Science Ltd.

The modified Julia olefination in vitamin D2 synthesis

A partial synthesis of vitamin D2 employing fragments derived from a new improved degradation procedure is described. The 7,8-double bond of the vitamin D triene system was synthesised via the modified Julia olefination. The new procedure is more efficient than the classical Julia olefination.