(8R,9S,13S,14S,17R)-17-ethynyl-2-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol

Base Information

• Chemical Name: (8R,9S,13S,14S,17R)-17-ethynyl-2-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
• CAS No.: 22415-44-7
• Molecular Formula: C21H26 O3
• Molecular Weight: 326.436
• DSSTox Substance ID: DTXSID70945075
• Nikkaji Number: J528.981E
• Wikidata: Q82922313
• ChEMBL ID: CHEMBL1627649
• Mol file: 22415-44-7.mol

Synonyms:2-methoxyethinyl estradiol

Chemical Property of (8R,9S,13S,14S,17R)-17-ethynyl-2-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol

Chemical Property:

• Vapor Pressure: 7.21E-10mmHg at 25°C
• Refractive Index: 1.612
• Boiling Point: 476°Cat760mmHg
• Flash Point: 241.7°C
• PSA: 49.69000
• Density: 1.22g/cm³
• LogP: 3.62120
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Pyridine (Slightly), Methanol (Slightly)
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 326.18819469
• Heavy Atom Count: 24
• Complexity: 551

Purity/Quality:

95%+ or 98%+ ^*data from raw suppliers

2-Methoxy-17α-ethynylEstradiol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2(C#C)O)CCC4=CC(=C(C=C34)OC)O
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=CC(=C(C=C34)OC)O
• Uses: 2-Methoxy-17α-ethynyl Estradiol is a metabolite of the potent synthetic estrogen 17α-Ethynylestradiol (E685100).

Technology Process of (8R,9S,13S,14S,17R)-17-ethynyl-2-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol

There total 2 articles about (8R,9S,13S,14S,17R)-17-ethynyl-2-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-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:

mestranol (72-33-3) → ethinyl estradiol (57-63-6) + 2-hydroxy-mestranol (26011-40-5) + 17a-Ethynyl-2-methoxyestradiol (22415-44-7,26011-46-1) + [3H]-Ethinylestradiol glucuronide (60134-76-1) + 17-ethynyl-3-hydroxy-1,2,3(10)-estratrien-17β-yl-β-D-glucopyranosiduronate (75803-39-3) + 17-ethynyl-1,2,3(10)-estratrien-3,17β-diyl-β-D-glucopyranosiduronate (75812-41-8)

Guidance literature:

Product distribution; metabolism in women in dependence on geographic locality;

DOI:10.1016/0039-128X(80)90001-X

Reference yield:

2-methoxyestrone (362-08-3,7683-30-9) + lithium acetylide (70277-75-7) → 17a-Ethynyl-2-methoxyestradiol (22415-44-7,26011-46-1)

Guidance literature:

With ethylenediamine; In dimethyl sulfoxide;

DOI:10.1016/0039-128X(74)90150-0

Reference yield:

17a-Ethynyl-2-methoxyestradiol (22415-44-7,26011-46-1) → (8R,9S,13S,14S,17R)-3-(2,4-Dinitro-phenylazo)-17-ethynyl-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-2,17-diol

Guidance literature:

Multi-step reaction with 2 steps

1: BBr₃ / CH₂Cl₂

2: (i) aq. NaIO₄, AcOH, (ii) /BRN= 3636817/

With boron tribromide; In dichloromethane;

DOI:10.1016/0039-128X(74)90150-0

upstream raw materials:

2-methoxyestrone

lithium acetylide

mestranol

Downstream raw materials:

2-hydroxy-17α-ethynylestradiol