67337-15-9

Upstream product

• 67315-45-1 [5-Hydroxy-2-methylene-cyclohex-(Z)-ylidene]-acetic acid methyl ester 
• 144066-62-6 (4S)-(Z)-1-methylene-2-(1'-acetoxyethenyl-2')-4-hydroxycyclohexane 
• 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 
• 144066-59-1 (1S,4S)-1,1',4-trihydroxy-1-methyl-2-(ethenyl-2)-cyclohexan (2RS)-4-tetrahydropyranyl ether 
• 144066-58-0 (1S,7S)-7-hydroxy-1-methyl-2-oxabicyclo<4.3.0>non-4(5)-en-3-on (2RS)-7-tetrahydropyranyl ether 
• 144066-55-7 (1S,2'RS,4S)-1-methyl-2-(propyl-1')-1,2',3',4-tetrahydroxycyclohexa-2-en (2RS)-4-tetrahydropyranyl ether 
• 50-14-6 Calciferol 
• 55812-80-1 (1R,3aR,7aR)-7a-Methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-one 
• 50-14-6 vitamin D₂ 
• 144066-60-4 (1S,4S)-1,4-dihydroxy-1-methyl-2-(1'-acetoxyethenyl-2')-cyclohexane (2RS)-4-tetrahydropyranyl ether 
• 144066-54-6 (1S,4RS,8S)-4,8-dihydroxy-1-methyl-2-oxabicyclo<4.4.0>dec-6(7)-en-3-one (2RS)-8-tetrahydropyranyl ether 
• 144066-61-5 (4S)-(Z)-1-methylene-2-(1'-acetoxyethenyl-2')-4-hydroxycyclohexan (2RS)-4-tetrahydropyranyl ether 
• 144066-53-5 (1S,8S)-8-hydroxy-1-methyl-2-oxabicyclo<4.4.0>dec-6(7)-en-3-one (2RS)-8-tetrahydropyranyl ether 
• 144066-57-9 (1S,7S)-7-hydroxy-1-methyl-2-oxabicyclo<4.3.0>non-5(6)-en-3-on 7-tetrahydropyranyl ether 

Downstream Products

• 66251-15-8 Benzoic acid (S)-3-[2-hydroxy-eth-(Z)-ylidene]-4-methylene-cyclohexyl ester 
• 96685-53-9 (2Z)-2-<(5S)-5-(tert-butyldimethylsilyloxy)-2-methylene-cyclohexylidene>-ethanol 
• 100858-27-3 (S)-(Z)-{2-[5-(tert-butyldimethylsiloxy)-2-methylenecyclohexylidene]ethyl}diphenylphosphine oxide 
• 651734-12-2 20S-Hydroxyvitamin D₃ 
• 123836-63-5 <3S-(1Z,3α,5β)>-<2-<3-Fluoro-5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-methylenecyclohexylidene>ethyl>diphenylphosphine Oxide 
• 123836-62-4 <1R-(1β,3Z,5α)>-<<3-(2-Chloroethylidene)-5-fluoro-4-methylenecyclohexyl>oxy>(1,1-dimethylethyl)dimethylsilane 
• 123836-61-3 <3S-(1Z,3β,5α)>-<3-Fluoro-5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-methylenecyclohexylidene>ethanol 
• 1014718-14-9 C₃₇H₅₉⁽²⁾H₆FO₂Si₂ 
• 1014718-19-4 1α-tert-butyl-dimethyl-silanyloxy-3β-fluoro-25-trimethylsilanyloxy-16-ene-20-cyclopropyl-26,27-hexadeutero-cholecalciferol 
• 199798-99-7 C₃₈H₆₅FO₂Si₂ 
• 926315-13-1 benzoic acid (2R,3S,5R,7S)-7-((t-butyldimethyl)silanyloxy)-5-hydroxy-4-methylene-1-oxa-spiro[2.5]oct-2-yl methyl ester 
• 926315-20-0 benzoic acid (2R,3S,5S,7S)-7-((t-butyldimethyl)silanyloxy)-5-hydroxy-4-methylene-1-oxa-spiro[2.5]oct-2-yl methyl ester 
• 926315-15-3 benzoic acid 2-[(3S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-3-fluoro-2-methylene-cyclohex-(Z)-ylidene]-ethyl ester 
• 1014717-86-2 C₄₅H₆₉⁽²⁾H₆F₇O₃Si₃ 

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.

Probing the structural requirements for vitamin D3 inhibition of the hedgehog signaling pathway

A structure-activity relationship study to elucidate the structural basis for hedgehog (Hh) signaling inhibition by vitamin D3 (VD3) was performed. Functional and non-functional regions of VD3 and VD2 were obtained through straightforward synthetic means

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.

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.

Synthesis of Retiferol RAD1 and RAD2, the Lead Representatives of a New Class of des-CD Analogs of Cholecalciferol

The design and total convergent synthesis are described for the leading representatives of the new class of analogs of cholecalciferol with the CD-ring system replaced with a two-carbon aliphatic spacer.The leading representatives of C21 retiferols (RAD1

FRAGMENT A OF VITAMIN D3 FROM HAJOS ENEDIONE

Total synthesis of fragment A of vitamin D3 starting from optically active Hajos enedione (4) is described.