72696-49-2

Basic information

• Product Name: 24,24-difluoro-1,25-dihydroxyvitamin D3
• Synonyms: 24,24-difluoro-1,25-dihydroxyvitamin D3
• CAS NO: 72696-49-2
• Molecular Formula: C₂₇H₄₂F₂O₃
• Molecular Weight: 0
• Mol File: 72696-49-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 581.1°C at 760 mmHg
• Flash Point: 305.2°C
• Appearance: /
• Density: 1.12g/cm³
• Vapor Pressure: 6.37E-16mmHg at 25°C
• Refractive Index: 1.531
• CAS DataBase Reference: 24,24-difluoro-1,25-dihydroxyvitamin D3(CAS DataBase Reference)
• NIST Chemistry Reference: 24,24-difluoro-1,25-dihydroxyvitamin D3(72696-49-2)
• EPA Substance Registry System: 24,24-difluoro-1,25-dihydroxyvitamin D3(72696-49-2)

Safety Data

• Hazardous Substances Data: 72696-49-2(Hazardous Substances Data)

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

• 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 
• 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 
• 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 
• 143101-56-8 (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]-butyronitrile 

Relevant articles and documents

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 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.

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)].