80474-67-5

Basic information

• Product Name: 5-Iodomethyl 6a,9a-Difluoro-11-hydroxy-16a-methyl-3-oxo-17a-(propionyloxy)-androsta-1,4-diene-17-carbothioate
• Synonyms: 5-Iodomethyl 6a,9a-Difluoro-11-hydroxy-16a-methyl-3-oxo-17a-(propionyloxy)-androsta-1,4-diene-17-carbothioate;5-Iodomethyl 6α,9α-Difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-(propionyloxy)-androsta-1,4-diene-17β-carbothioate;(6α,11,16α,17α)-6,9-Difluoro-11-hydroxy-16-Methyl-3-oxo-17-(1-oxopropoxy)-androsta-1,4-diene-17-carbothioic Acid S-(IodoMethyl) Ester
• CAS NO: 80474-67-5
• Molecular Formula: C₂₅H₃₁F₂IO₅S
• Molecular Weight: 608.4769164
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
• Mol File: 80474-67-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 606.721°C at 760 mmHg
• Flash Point: 320.733°C
• Appearance: /
• Density: 1.553g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.599
• Solubility: Chloroform, Dichloromethane, DMF, Ethanol, Ethyl Acetate, Methanol
• CAS DataBase Reference: 5-Iodomethyl 6a,9a-Difluoro-11-hydroxy-16a-methyl-3-oxo-17a-(propionyloxy)-androsta-1,4-diene-17-carbothioate(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Iodomethyl 6a,9a-Difluoro-11-hydroxy-16a-methyl-3-oxo-17a-(propionyloxy)-androsta-1,4-diene-17-carbothioate(80474-67-5)
• EPA Substance Registry System: 5-Iodomethyl 6a,9a-Difluoro-11-hydroxy-16a-methyl-3-oxo-17a-(propionyloxy)-androsta-1,4-diene-17-carbothioate(80474-67-5)

Safety Data

• Hazardous Substances Data: 80474-67-5(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

Different sources of media describe the Uses of 80474-67-5 differently. You can refer to the following data:
1. An intermediate in the synthesis of Fluticasone Propionate
2. An intermediate in the synthesis of Fluticasone Propionate.

InChI:InChI=1/C25H31F2IO5S/c1-5-20(31)33-25(21(32)34-12-28)13(2)8-15-16-10-18(26)17-9-14(29)6-7-22(17,3)24(16,27)19(30)11-23(15,25)4/h6-7,9,13,15-16,18-19,30H,5,8,10-12H2,1-4H3/t13?,15?,16-,18?,19-,22-,23-,24?,25?/m0/s1

Upstream product

• 80486-69-7 S-chloromethyl 6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-propionyloxyandrosta-1,4-diene-17β-carbothioate 
• 192191-50-7 Propionic acid (6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-(toluene-4-sulfonyloxymethylsulfanylcarbonyl)-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl ester 
• 65429-42-7 6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-(propionyloxy)androsta-1,4-diene-17β-carboxylic acid 
• 80473-92-3 6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxo-androsta-1,4-diene-17β-carbothioic acid 
• 28416-82-2 6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxylic acid 
• 80474-45-9 17-propionate carbothioic acid 
• 577965-09-4 Propionic acid (6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-propionylsulfanylcarbonyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl ester 
• 105638-31-1 17β-[(N,N-dimethylcarbamoyl)thio]formyl-6α,9α-difluoro-11β-hydroxy-16α-methyl-17α-propionyloxy-3-one androstone-1,4-diene 

Downstream Products

• 80474-14-2 flixotide 
• 192191-50-7 Propionic acid (6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-(toluene-4-sulfonyloxymethylsulfanylcarbonyl)-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl ester 

Relevant articles and documents

NOVEL PROCESS AND INTERMEDIATES

The present invention relates to a process for the preparation of steroidal 17β-carboxylic thioates. More particularly the present invention relates to a convenient and efficient synthesis of steroidal 17β-carboxylic thioates, such as fluticasone propionate I, using soluble mixed fluorides to introduce fluorine by displacing an appropriate leaving group X in compounds II resulting in selective and controlled fluorination. The present invention also relates to intermediates II and their preparation.

Automated radiosynthesis of no-carrier-added [S-fluoromethyl-18F] fluticasone propionate as a radiotracer for lung deposition studies with PET

Fluticasone propionate [(S)-fluoromethyl-6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α -(propionyloxy)-androsta-1,4-diene-17β-carbothioate; FP] is a potent anti-inflammatory steroid with several therapeutic indications, including use as an anti-asthmatic drug when administered as sized particles by inhalation from a pressurised metered-dose inhaler (pMDI). FP was successfully labelled with fluorine-18 (t( 1/4 ) = 109.6 min: β+ = 100%) by displacement of tosylate with cyclotron-produced no-carrier-added [18F]fluoride in an (S)-tosylmethyl precursor prepared from the known (S)-chloromethyl analogue of FP. Radiochemically pure [S-/fluoromethyl-18]FP was separated by reverse phase HPLC in 35% radiochemical yield (decay-corrected) within 80 min from the end of radionuclide production (as verified by, radio-HPLC, LC-MS and LC-NMR). The radiosynthesis was automated for the safe production of high radioactivities (20-50 mCi) of [18F]FP in a lead-shielded hot-cell for subsequent incorporation into formulated FP particles within a pMDI and subsequent study of FP deposition in human lung using positron emission tomography (PET).