(13S)-3-(benzyloxy)-13-methyl-6,7,8,9,11,12,13,14-octahydro-17H-cyclopenta[a]phenanthren-17-one

Base Information

• Chemical Name: (13S)-3-(benzyloxy)-13-methyl-6,7,8,9,11,12,13,14-octahydro-17H-cyclopenta[a]phenanthren-17-one
• CAS No.: 138743-03-0
• Molecular Formula: C25H26O2
• Molecular Weight: 358.48
• European Community (EC) Number: 844-242-2
• DSSTox Substance ID: DTXSID00568155
• Wikidata: Q82454327
• Mol file: 138743-03-0.mol

Synonyms:138743-03-0;3-O-Benzyl 15,16-Dehydro Estrone;(13S)-3-(benzyloxy)-13-methyl-6,7,8,9,11,12,13,14-octahydro-17H-cyclopenta[a]phenanthren-17-one;(8R,9S,13S,14S)-3-(Benzyloxy)-13-methyl-7,8,9,11,12,13-hexahydro-6H-cyclopenta[a]phenanthren-17(14H)-one;(8R,9S,13S,14S)-13-methyl-3-phenylmethoxy-7,8,9,11,12,14-hexahydro-6H-cyclopenta[a]phenanthren-17-one;3-(Benzyloxy)estra-1,3,5(10),15-tetraen-17-one;SCHEMBL2565874;3-(Benzyloxy)-estra-1,3,5(10),15-tetraen-17-one;DTXSID00568155;UJOCQXHOSBJACO-AHCIIZGASA-N;AKOS026675651;SS-3378;3-Benzyloxyestra-1,3,5(10),15-tetraen-17-one

Chemical Property of (13S)-3-(benzyloxy)-13-methyl-6,7,8,9,11,12,13,14-octahydro-17H-cyclopenta[a]phenanthren-17-one

Chemical Property:

• PSA: 26.30000
• LogP: 5.46680
• Solubility.: Chloroform
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 358.193280068
• Heavy Atom Count: 27
• Complexity: 589

Purity/Quality:

99% ^*data from raw suppliers

3-O-Benzyl15,16-DehydroEstrone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1C=CC2=O)CCC4=C3C=CC(=C4)OCC5=CC=CC=C5
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1C=CC2=O)CCC4=C3C=CC(=C4)OCC5=CC=CC=C5
• Uses: Intermediate in the preparation of Estratrienes.

Technology Process of (13S)-3-(benzyloxy)-13-methyl-6,7,8,9,11,12,13,14-octahydro-17H-cyclopenta[a]phenanthren-17-one

There total 9 articles about (13S)-3-(benzyloxy)-13-methyl-6,7,8,9,11,12,13,14-octahydro-17H-cyclopenta[a]phenanthren-17-one 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: 52.0%

3-benzyloxy-17,17-ethylenedioxyestra-1,3,5(10),15-tetraene (534572-67-3) → (14α)-3-benzyloxy-1,3,5(10),15-estratetraen-17-one (138743-03-0)

Guidance literature:

With toluene-4-sulfonic acid; In water; acetone; at 20 ℃; for 1.5h;

DOI:10.1021/jm0204340

Reference yield:

3-benzyloxy-17-trimethylsilyloxy-estra-1,3,5(10),16-tetraene (213819-19-3) → (14α)-3-benzyloxy-1,3,5(10),15-estratetraen-17-one (138743-03-0)

Guidance literature:

With oxygen; palladium diacetate; In dichloromethane; dimethyl sulfoxide; at 35 ℃; Product distribution / selectivity;

Reference yield:

3-benzyloxyestra-1,3,5(10)-trien-17-one (858-98-0) → (14α)-3-benzyloxy-1,3,5(10),15-estratetraen-17-one (138743-03-0)

Guidance literature:

Multi-step reaction with 4 steps

1: p-TSA

2: pyridine*HBr₃

3: t-BuOK / dimethylsulfoxide

4: p-TSA / acetone; H₂O

With pyridinium perbromide hydrobromide; potassium tert-butylate; toluene-4-sulfonic acid; In water; dimethyl sulfoxide; acetone;

DOI:10.1016/S0040-4020(01)81933-5

upstream raw materials:

3-benzyloxy-17,17-ethylenedioxyestra-1,3,5⁽¹⁰⁾,15-tetraene

benzyl bromide

3-benzyloxyestra-1,3,5⁽¹⁰⁾-trien-17-one

17,17-ethylenedioxy-3-benzyloxy-estra-1,3,5 ⁽¹⁰⁾-trien-17-one

Downstream raw materials:

15α-hydroxyestriol

17β-acetyloxy-3-benzyloxy-estra-1,3,5(10),15-tetraene

17-acetyl-3-benzyl estetrol

17-acetyl estetrol