72696-49-2

Usage

Type

Synthetic analog of the active form of vitamin D.

Increased potency

Compared to natural vitamin D, it has higher potency.

Stability

Enhanced stability compared to natural vitamin D.

Therapeutic potential

Candidate for treatment of various diseases, such as osteoporosis and certain types of cancer.

Mechanism of action

Binds to the vitamin D receptor.

Regulation

Regulates calcium and phosphorus metabolism.

Cellular effects

Exerts anti-proliferative and pro-differentiation effects on cells.

Research status

Ongoing research and clinical trials due to promising results in potential medical applications.

InChI:InChI=1/C27H42F2O3/c1-17(12-14-27(28,29)25(3,4)32)22-10-11-23-19(7-6-13-26(22,23)5)8-9-20-15-21(30)16-24(31)18(20)2/h8-9,17,21-24,30-32H,2,6-7,10-16H2,1,3-5H3/b19-8+,20-9-/t17-,21+,22-,23+,24-,26-/m1/s1

Upstream product

• 74016-73-2 24,24-difluorocholesta-5,7-dien-1α,3β,25-triol 
• 114694-13-2 Toluene-4-sulfonic acid (S)-2-{(R)-4-[2-[(3S,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl ester 
• 114694-13-2 Toluene-4-sulfonic acid (S)-2-{(R)-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}-propyl ester 
• 143884-27-9 (R)-5-{(R)-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}-2,2-difluoro-hexanoic acid methyl ester 
• 144907-43-7 (R)-5-{(R)-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}-2-oxo-hexanoic acid methyl ester 
• 131496-31-6 (R)-3-{(R)-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}-butyraldehyde 
• 143884-28-0 (R)-6-{(R)-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}-3,3-difluoro-2-methyl-heptan-2-ol 
• 143101-52-4 1α,3β-bis<(tert-butyldimethylsilyl)oxy>-23,24-bisnorchol-15,16-dien-22-ol 
• 150054-30-1 Oxalic acid (R)-3-[(1S,3R,9S,10R,13R,14R,17R)-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1-(ethoxycarbonyl-difluoro-methyl)-butyl ester methyl ester 
• 126771-94-6 Toluene-4-sulfonic acid (S)-2-[(1S,3R,9S,10R,13R,14R,17R)-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-propyl ester 
• 150283-03-7 (R)-5-[(1S,3R,9S,10R,13R,14R,17R)-1,3-Bis-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2,2-difluoro-3-hydroxy-hexanoic acid ethyl ester 
• 143101-54-6 ethyl 24,24-difluoro-1α,3β-bis<(tert-butyldimethylsilyl)oxy>homochol-5,7-dien-25-oate 
• 143101-55-7 24,24-difluoro-1α,3β-bis<(tert-butyldimethylsilyl)oxy>cholesta-5,7-dien-25-ol 
• 143101-50-2 1α,3β-bis<(tert-butyldimethylsilyl)oxy>-24-norchol-5,7-dien-23-al 

Relevant academic research and scientific papers

An improved synthesis of 24,24-difluoro-1α,25-dihydroxyvitamin D3 from readily available vitamin D2

An improved synthesis of a highly potent vitamin D3 analog, 24,24-difluoro-1α,25-dihydroxyvitamin D3 (1b) has been accomplished via vitamin D2-SO2 adducts. The introduction of fluorine atoms was performed by tre

An alternative and efficient synthesis of 24,24-difluoro-1α,25-dihydroxyvitamin D3

An alternative synthesis of the title compound 2, a highly potent analog of 1α,25-dihydroxyvitamin D3 (1), is described. Starting with 1α,3β-bis[(tert-butyldimethylsilyl)oxy]androst-5-ene (8), 2 was obtained in 3.8% total yield through 10 steps. This method provides compound 2 in much higher yield than that reported previously.

An improved synthesis of 24,24-difluoro-1α,25-dihydroxy-vitamin D3 from vitamin D2

An improved synthesis of a highly potent vitamin D3 analog, 24,24-difluoro-1α,25-dihydroxyvitamin D3 has been accomplished. The total yield was 9.3% from inexpensive vitamin D2 in 11 steps.

Immunosuppressive agents

The invention relates to pharmaceutical compositions comprising at least one Vitamin D derivative and a method of using the pharmaceutical compositions in suppressing immune responses.

Process for the preparation of 24,24-difluoro-1α,25-dihydroxy vitamin D3 and intermediates obtained therefrom

The present invention relates to a process and intermediates for the preparation of 24,24-difluoro-1α,25-dihydroxycholecalciferol from the readily-available 1α,3β-dihydroxyandrost-5-en-17-one which is made by a known microbiological process from 3β-hydroxyandrost-5-en-17-one [R. M. Dodson, A. H. Goldkamp and R. D. Muir, J. Amer. Chem. Soc. 82 4026 (1960)].

Method of treatment

The present invention relates to a method of treating osteoporosis by administering to a host suffering from osteoporosis an effective amount of 24,24-difluoro-1α,25-dihydroxycholecalciferol.