(3S,5R,6R,7R,8R,9S,10R,13S,14S,15S,16S,17S)-Octadecahydro-17-(3-hydroxy-1-propynyl)-10,13-dimethyl-5hdicyclopropa(6,7:15,16)cyclopenta(a)phenanthrene-3,5,17-triol

Base Information

• Chemical Name: (3S,5R,6R,7R,8R,9S,10R,13S,14S,15S,16S,17S)-Octadecahydro-17-(3-hydroxy-1-propynyl)-10,13-dimethyl-5hdicyclopropa(6,7:15,16)cyclopenta(a)phenanthrene-3,5,17-triol
• CAS No.: 82543-17-7
• Molecular Formula: C24H34O4
• Molecular Weight: 386.532
• European Community (EC) Number: 617-349-5
• DSSTox Substance ID: DTXSID20517428
• Wikidata: Q76423021
• Mol file: 82543-17-7.mol

Synonyms:82543-17-7;EC 617-349-5;(1R,2R,4R,5R,7S,10R,11S,14S,15S,16S,18S,19S)-15-(3-Hydroxyprop-1-ynyl)-10,14-dimethylhexacyclo[9.8.0.02,4.05,10.014,19.016,18]nonadecane-5,7,15-triol;(3S,5R,6R,7R,8R,9S,10R,13S,14S,15S,16S,17S)- Octadecahydro-17-(3-hydroxy-1-propynyl)-10,13-dimethyl-5hdicyclopropa( 6,7:15,16)cyclopenta(a)phenanthrene-3,5,17-triol;(3S,5R,6R,7R,8R,9S,10R,13S,14S,15S,16S,17S)-octadecahydro-17-(3-hydroxy-1-propynyl)-10,13-dimethyl-5H-dicyclopropa[6,7;SCHEMBL13936419;DTXSID20517428;NS00005875;17-(3-Hydroxy-1-propynyl)-6?,7?:15?,16?-dimethyleneandrostane-3?,5?,17?-triol;17-(3-Hydroxy-1-propynyl)-6beta,7beta:15beta,16beta-dimethyleneandrostane-3beta,5beta,17beta-triol

Chemical Property of (3S,5R,6R,7R,8R,9S,10R,13S,14S,15S,16S,17S)-Octadecahydro-17-(3-hydroxy-1-propynyl)-10,13-dimethyl-5hdicyclopropa(6,7:15,16)cyclopenta(a)phenanthrene-3,5,17-triol

Chemical Property:

• Vapor Pressure: 0Pa at 25℃
• PSA: 80.92000
• LogP: 1.94350
• Solubility.: Chloroform, Methanol
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 386.24570956
• Heavy Atom Count: 28
• Complexity: 797

Purity/Quality:

99.9% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(CC1(C3CC3C4C2CCC5(C4C6CC6C5(C#CCO)O)C)O)O
• Isomeric SMILES: C[C@]12CC[C@@H](C[C@]1([C@@H]3C[C@@H]3[C@@H]4[C@@H]2CC[C@]5([C@H]4[C@@H]6C[C@@H]6[C@]5(C#CCO)O)C)O)O
• Uses: Intermediate for the preparation of Drospirenone.

Technology Process of (3S,5R,6R,7R,8R,9S,10R,13S,14S,15S,16S,17S)-Octadecahydro-17-(3-hydroxy-1-propynyl)-10,13-dimethyl-5hdicyclopropa(6,7:15,16)cyclopenta(a)phenanthrene-3,5,17-triol

There total 9 articles about (3S,5R,6R,7R,8R,9S,10R,13S,14S,15S,16S,17S)-Octadecahydro-17-(3-hydroxy-1-propynyl)-10,13-dimethyl-5hdicyclopropa(6,7:15,16)cyclopenta(a)phenanthrene-3,5,17-triol 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: 78.0%

propargyl alcohol (107-19-7) + (2S,4aR,4bS,6aS,7aS,8aS,8bS,8cR,8dR,9aR,9bR)-2,9b-dihydroxy-4a,6a-dimethyloctadecahydro-7H-cyclopropa[4,5]cyclopenta[1,2-a]cyclopropa[l]phenanthren-7-one (82543-16-6) → 17α-(3-hydroxy-1-propinyl)-6β,7β;15β,16β-dimethylene-5β-androstane-3β,5,17β-triol (82543-17-7)

Guidance literature:

propargyl alcohol; (2S,4aR,4bS,6aS,7aS,8aS,8bS,8cR,8dR,9aR,9bR)-2,9b-dihydroxy-4a,6a-dimethyloctadecahydro-7H-cyclopropa[4,5]cyclopenta[1,2-a]cyclopropa[l]phenanthren-7-one; With potassium tert-butylate; In tetrahydrofuran; at 0 - 5 ℃;

With water; acetic acid; In tetrahydrofuran; Product distribution / selectivity;

Reference yield:

hydroxy-1-propyne (6175-54-8) + (2S,4aR,4bS,6aS,7aS,8aS,8bS,8cR,8dR,9aR,9bR)-2,9b-dihydroxy-4a,6a-dimethyloctadecahydro-7H-cyclopropa[4,5]cyclopenta[1,2-a]cyclopropa[l]phenanthren-7-one (82543-16-6) → 17α-(3-hydroxy-1-propinyl)-6β,7β;15β,16β-dimethylene-5β-androstane-3β,5,17β-triol (82543-17-7)

Guidance literature:

With potassium methanolate; In tetrahydrofuran; at 0 - 35 ℃; Inert atmosphere;

Reference yield:

3β-hydorxy-15β,16β-methylene androst-5-ene-17-one (67372-65-0) → 17α-(3-hydroxy-1-propinyl)-6β,7β;15β,16β-dimethylene-5β-androstane-3β,5,17β-triol (82543-17-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 55 percent / Botryodiplodia malorum / 40 h

2: 65 percent / dimethylaminopyridine / pyridine / 72 h / Ambient temperature

3: 98 percent / tert-butylhydroperoxide, VO(C₅H₇O₂)2 / toluene / 2 h / 80 °C

4: 79 percent / P(C₆H₅)3 / CCl₄; CH₂Cl₂; pyridine / 2 h / 0 deg C to room temp.

5: 75 percent / Zn / acetic anhydride; tetrahydrofuran / 1.5 h / 70 °C

6: 94 percent / KOH, NaClO₄ / tetrahydrofuran; methanol / 2.5 h / Ambient temperature

7: 88 percent / Zn/Cu / 1,2-dimethoxy-ethane / 5 h / 55 °C

8: 69 percent / KOEt / tetrahydrofuran / 2 h / Ambient temperature

With tert.-butylhydroperoxide; dmap; potassium hydroxide; Botryodiplodia malorum; VO(C₅H₇O₂)2; potassium ethoxide; sodium perchlorate; copper; triphenylphosphine; zinc; In tetrahydrofuran; pyridine; methanol; tetrachloromethane; 1,2-dimethoxyethane; dichloromethane; acetic anhydride; toluene;

upstream raw materials:

propargyl alcohol

(2S,4aR,4bS,6aS,7aS,8aS,8bS,8cR,8dR,9aR,9bR)-2,9b-dihydroxy-4a,6a-dimethyloctadecahydro-7H-cyclopropa[4,5]cyclopenta[1,2-a]cyclopropa[l]phenanthren-7-one

3β-hydorxy-15β,16β-methylene androst-5-ene-17-one

3β,5-dihydroxy-15β,16β-methylene-5β-androst-6-en-17-one

Downstream raw materials:

5β-hydroxy-3-carbonyl-6β,7β,5β,16β-dimethylene-17α-pregna-21,17-carboxylactone

6β,7β;15β,16β-dimethylene-3β,5β-dihydroxy-17α-pregn-21,17-carbolactols

17α-(3-hydroxypropyl)-6β,7β;15β,16β-dimethylene-5β-androstane-3β,5,17β-triol

Spirorenone

Refernces

• 1、 -. "A PROCESS FOR PREPARING DROSPIRENONE AND INTERMEDIATE THEREOF". Page/Page column 16. . Retrieved 2009/01/20.
• 2、 -. "A process for the preparation of drospirenone". Page/Page column 4; 9; 15. . Retrieved 2010/02/13.