S-(fluoromethyl) 6,9-difluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthrene-17-carbothioate

Base Information

• Chemical Name: S-(fluoromethyl) 6,9-difluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthrene-17-carbothioate
• CAS No.: 90566-53-3
• Molecular Formula: C₂₂H₂₇F₃O₄S
• Molecular Weight: 444.515
• European Community (EC) Number: 892-507-6
• DSSTox Substance ID: DTXSID30861121
• Wikipedia: Fluticasone
• Mol file: 90566-53-3.mol

Synonyms:90566-53-3;DTXSID30861121;BCP31287;NS00009614;S-(Fluoromethyl) 6,9-difluoro-11,17-dihydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carbothioate

Chemical Property of S-(fluoromethyl) 6,9-difluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthrene-17-carbothioate

Chemical Property:

• Melting Point: -18.1oC
• Boiling Point: 553.2 °C at 760 mmHg
• PKA: 11.66±0.70(Predicted)
• Flash Point: 288.4 °C
• PSA: 105.97000
• Density: 1.37 g/cm³
• LogP: 4.43000
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Acetonitrile (Slightly), Chloroform (Slightly)
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 444.15821500
• Heavy Atom Count: 30
• Complexity: 861

Purity/Quality:

99% ^*data from raw suppliers

Fluticasone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC2C3CC(C4=CC(=O)C=CC4(C3(C(CC2(C1(C(=O)SCF)O)C)O)F)C)F
• Recent EU Clinical Trials: A prospective, multicenter, 12-week, randomized open-label study to evaluate the efficacy and safety of glycopyrronium (50 micrograms o.d.) or indacaterol maleate and glycopyrronium bromide fixed-dose combination (110/50 micrograms o.d.) regarding symptoms and health status in patients with moderate chronic obstructive pulmonary disease (COPD) switching from treatment with any standard COPD regimen
• Uses: therapeutic for asthma and allergic rhinitis Flonase Fluticasone is an inhaled corticosteroid used in the treatment of respiratory diseases.

Technology Process of S-(fluoromethyl) 6,9-difluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthrene-17-carbothioate

There total 2 articles about S-(fluoromethyl) 6,9-difluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthrene-17-carbothioate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

S-iodomethyl 6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate (1174034-80-0) → fluticasone (90566-53-3)

Guidance literature:

With silver fluoride; In acetonitrile; at 20 ℃; for 3h; Darkness;

DOI:10.1080/00304940809458122

Reference yield: 35.0%

S-hydroxymethyl 6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate → fluticasone (90566-53-3)

Guidance literature:

With (bis-(2-methoxyethyl)amino)sulfur trufluoride; In dichloromethane; at 60 ℃; for 0.166667h;

Reference yield:

fluticasone (90566-53-3) → 6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-(propionyloxy)androsta-1,4-diene-17β-carboxylic acid (65429-42-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: water; periodic acid / tetrahydrofuran / 3 h / 20 °C

2.1: triethylamine / acetone / 2 h / 20 - 60 °C

2.2: 1 h / 30 °C

With water; periodic acid; triethylamine; In tetrahydrofuran; acetone;

upstream raw materials:

S-iodomethyl 6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate

Downstream raw materials:

6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-(propionyloxy)androsta-1,4-diene-17β-carboxylic acid

Refernces

• 1、 -. "17.BETA- (ALPHA-HYDROXY) -ESTERS OF ANDROSTANES AS INTERMEDIATES FOR THE PREPARATION FOR THE PREPARATION OF 17Β-FLUORINATED-ANDROSTANE ESTERS". Page 31-32. . Retrieved 2008/06/13.