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 
• 131852-63-6 (5Z,22E)-(7R)-3β-(tert-butyldimethylsilyloxy)-9,10-seco-8α-ergosta-5,10(19),22-triene-7,8-diol 
• 50-14-6 Calciferol 
• 56282-28-1 vitamin D₂ 5,6-diol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 84985-78-4 (4R,7aR)-1-((2R,5R,E)-5,6-dimethylhept-3-en-2-yl)-4-((R,Z)-1-hydroxy-2-((S)-5-hydroxy-2-methylenecyclohexylidene)ethyl)-7a-methyloctahydro-1H-inden-4-ol 
• 84927-66-2 7,8-dihydroxy-7,8-dihydrovitamin D₃ 
• 1014717-75-9 (S,Z)-tert-butyl(2-(5-((tert-butyldimethylsilyl)oxy)-2-methylenecyclohexylidene)ethoxy)dimethylsilane 
• 104846-62-0 3(S)-tert-butyldimethylsilyloxy-9,10-secoergosta-5,7(E),10⁽¹⁹⁾,22(E)-tetraene 
• 935-79-5 cis-1,2,3,6-tetrahydrophthalic anhydride 

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 
• 869101-36-0 (1R,3aR,5S,7aR)-5-{2-[(S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-ethyl}-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-4-one 
• 869101-43-9 {(S)-3-[2-[(1R,3aR,4S,5S,7aR)-4-Allyl-1-((R)-1,5-dimethyl-hexyl)-4-methoxy-7a-methyl-octahydro-inden-5-yl]-eth-(Z)-ylidene]-4-methylene-cyclohexyloxy}-tert-butyl-dimethyl-silane 
• 869101-32-6 (1R,3aR,4S,5S,7aR)-4-Allyl-5-{2-[(S)-5-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-ethyl}-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-4-ol 
• 50-14-6 Calciferol 
• 247900-07-8 (7Z)-Vitamin D₂ 
• 67-97-0 vitamin D₃ 
• 87649-55-6 tert-Butyl-{(S)-3-[2-[(1R,3aS,7aR)-1-(1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-methylene-cyclohexyloxy}-dimethyl-silane 
• 96685-54-0 Acetic acid 1-[(1R,3aR,7aR)-4-benzenesulfonyl-1-(1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-4-yl]-2-[(S)-5-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-ethyl ester 
• 100858-27-3 (S)-(Z)-{2-[5-(tert-butyldimethylsiloxy)-2-methylenecyclohexylidene]ethyl}diphenylphosphine oxide 
• 84927-61-7 23-oxa-25-hydroxyvitamin D₃ 

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.

On the Julia Alkenylation reaction in vitamin D synthesis. Isolation of four geometrical isomers of vitamin D4

Coupling of sulfone 2 and aldehyde 3b using the Julia alkenylation procedure has been reexamined using modern product separation techniques. It was found that vitamin D4 1b and its geometric isomers 10, 11 and 12 are formed in a ratio of 75:10:10:5, respectively. The building blocks 2 and 3b were prepared from vitamin D2. Correlations for the structure assignment of vitamin D stereoisomers by 1H NMR spectroscopy are presented.