(1S,9R,11S,14S,15S)-15-methyl-9-[9-(4,4,5,5,5-pentafluoropentanesulfinyl)nonyl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol

Base Information

• Chemical Name: (1S,9R,11S,14S,15S)-15-methyl-9-[9-(4,4,5,5,5-pentafluoropentanesulfinyl)nonyl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol
• CAS No.: 129453-61-8
• Molecular Formula: C32H47F5O3S
• Molecular Weight: 606.781
• Hs Code.: 2937230000
• ChEMBL ID: CHEMBL1712246
• Mol file: 129453-61-8.mol

Synonyms:SR-01000597471;NCGC00024964-02;Curator_000010;CHEMBL1712246;SCHEMBL20448785;VWUXBMIQPBEWFH-LQKBAPIOSA-N;HMS3412C11;HMS3676C11;AMY38947;AKOS024456349;SR-01000597471-1;SR-01000597471-2;Z2588038967;(1S,9R,11S,14S,15S)-15-methyl-9-[9-(4,4,5,5,5-pentafluoropentanesulfinyl)nonyl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol;(1S,9R,11S,14S,15S)-15-methyl-9-{9-[(4,4,5,5,5-pentafluoropentane)sulfinyl]nonyl}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol

Chemical Property of (1S,9R,11S,14S,15S)-15-methyl-9-[9-(4,4,5,5,5-pentafluoropentanesulfinyl)nonyl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 3.95E-19mmHg at 25°C
• Melting Point: 104-106°C
• Refractive Index: 1.521
• Boiling Point: 674.8 °C at 760 mmHg
• PKA: 10.27±0.70(Predicted)
• Flash Point: 361.9 °C
• PSA: 76.74000
• Density: 1.201 g/cm³
• LogP: 9.54830
• Storage Temp.: 2-8°C
• Solubility.: DMSO: >5mg/mL
• XLogP3: 9.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 14
• Exact Mass: 606.31660734
• Heavy Atom Count: 41
• Complexity: 854

Purity/Quality:

99%, ^*data from raw suppliers

Fulvestrant ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2O)C(CC4=C3C=CC(=C4)O)CCCCCCCCCS(=O)CCCC(C(F)(F)F)(F)F
• Isomeric SMILES: C[C@]12CC[C@H]3C([C@@H]1CC[C@@H]2O)[C@@H](CC4=C3C=CC(=C4)O)CCCCCCCCCS(=O)CCCC(C(F)(F)F)(F)F
• General Description: Fulvestrant, also known as Faslodex, is a selective estrogen receptor downregulator used in the treatment of advanced breast cancer. Its commercial-scale synthesis involves stereoselective organocuprate addition and copper-mediated aromatization, with careful control of impurities and noncrystalline intermediates to ensure high-quality production. The process optimizes efficiency and cost while maintaining rigorous quality standards for the drug substance.

Technology Process of (1S,9R,11S,14S,15S)-15-methyl-9-[9-(4,4,5,5,5-pentafluoropentanesulfinyl)nonyl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol

There total 57 articles about (1S,9R,11S,14S,15S)-15-methyl-9-[9-(4,4,5,5,5-pentafluoropentanesulfinyl)nonyl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol 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: 95.0%

(+)-(7α)-[9-(4,4,5,5,5-pentafluoropentylsulfanyl)nonyl]estra-1,3,5(10)-triene-3,17β-diol (153004-31-0) → fulvestrant (129453-61-8,1316849-17-8,1807900-80-6,407577-53-1)

Guidance literature:

With dihydrogen peroxide; acetic acid; In water; ethyl acetate; at 40 ℃; for 4h; Inert atmosphere; Schlenk technique;

DOI:10.1039/c5cc05805h

Reference yield: 82.0%

7β-[9-(4,4,5,5,5-pentafluoropentylsulfanyl)nonyl]estra-1,3,5-trien-3,17β-diol → fulvestrant (129453-61-8,1316849-17-8,1807900-80-6,407577-53-1)

Guidance literature:

With dihydrogen peroxide; acetic acid; In ethyl acetate;

Reference yield: 32.0%

(7R,13S)-3-methoxy-13-methyl-7-(9-(4,4,5,5,5-pentafluoropentylsulfinyl)nonyl)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ol (1221256-46-7) → fulvestrant (129453-61-8,1316849-17-8,1807900-80-6,407577-53-1)

Guidance literature:

With aluminum (III) chloride; thiourea; In dichloromethane; at 20 - 55 ℃; Product distribution / selectivity;

upstream raw materials:

(+)-(7α)-[9-(4,4,5,5,5-pentafluoropentylsulfanyl)nonyl]estra-1,3,5(10)-triene-3,17β-diol

fulvestrant 17β-acetate

(7R,13S)-3-methoxy-13-methyl-7-(9-(4,4,5,5,5-pentafluoropentylsulfinyl)nonyl)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ol

4,4,5,5,5-pentafluorpentan-1-ol

Downstream raw materials:

fulvestrant 17β-acetate

ICI 182,780-17-ketone

(+)-(7α)-[9-(4,4,5,5,5-pentafluoropentylsulfanyl)nonyl]estra-1,3,5(10)-triene-3,17β-diol

Refernces

Fulvestrant: From the laboratory to commercial-scale manufacture

10.1021/op900315j

The study focuses on the development of a commercial manufacturing process for fulvestrant, the active ingredient in 'Faslodex', an estrogen-receptor downregulator used for treating advanced breast cancer. Key steps in the synthesis include a stereoselective 1,6-addition of an organocuprate to a steroidal dienone and copper-mediated aromatisation of the A-ring. The process involves managing noncrystalline intermediates and controlling the formation of key impurities to ensure drug substance quality. Chemicals used include fulvestrant, organocuprate, steroidal dienone, copper reagents, and various starting materials and solvents such as 19Nortestosterone, 1,1,9-nonanediol, pentafluoropentanol, and pentafluoroethyl iodide. These chemicals serve as starting materials, reagents, or intermediates in the synthesis of fulvestrant, with the aim of optimizing the production process for efficiency, cost-effectiveness, and quality control.

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