3 beta,5 beta-Dihydroxy-15 beta,16 beta-methylene-5 beta-androst-6-en-17-one

Base Information

• Chemical Name: 3 beta,5 beta-Dihydroxy-15 beta,16 beta-methylene-5 beta-androst-6-en-17-one
• CAS No.: 82543-15-5
• Molecular Formula: C20H28O3
• Molecular Weight: 316.441
• European Community (EC) Number: 617-346-9
• DSSTox Substance ID: DTXSID60517427
• Wikidata: Q72464832
• Mol file: 82543-15-5.mol

Synonyms:82543-15-5;3beta,5-Dihydroxy-15beta,16beta-methylene-5beta-androst-6-en-17-one;(3b,5b,15a,16a)-15,16-Dihydro-3,5-dihydroxy-3'H-cycloprop[15,16]androsta-6,15-dien-17-one;3 beta,5 beta-Dihydroxy-15 beta,16 beta-methylene-5 beta-androst-6-en-17-one;EC 617-346-9;3'H-Cycloprop[15,16]androsta-6,15-dien-17-one,15,16-dihydro-3,5-dihydroxy-, (3b,5b,15a,16a)-;(1R,2S,3S,5S,7S,10S,11R,14S,16R)-14,16-dihydroxy-7,11-dimethylpentacyclo[8.8.0.02,7.03,5.011,16]octadec-17-en-6-one;3|A,5|A-dihydroxy-15|A,16|A-methylene-androst-6-en-17-one;IYCDFUCBUZDDIU-MBYPHNFESA-N;3'H-Cycloprop[15,16]androsta-6,15-dien-17-one, 15,16-dihydro-3,5-dihydroxy-, (3?,5?,15?,16?)-;3?,5-Dihydroxy-15?,16?-methylene-5?-androst-6-en-17-one;3|A,5-Dihydroxy-15|A,16|A-methylene-5|A-androst-6-en-17-one;SCHEMBL856974;3beta,5beta-dihydroxy-15alpha,16alpha-methylene-androst-6-en-17-one;DTXSID60517427;AKOS016002260;AC-28720;DS-14178;CS-0158287;NS00011525;D95108;2-(4-(4-NITROPHENOXY)PHENYL)ACETICACID;A864390;Q-102811;3 ,5 -Dihydroxy-15 ,16 -methylene-androst-6-en-17-one;3b,5-Dihydroxy-15b,16b-methylene-5b-androst-6-en-17-one;3?,5?-Dihydroxy-15?,16?-methylene-5 ?-androst-6-en-17-one;3beta,5beta-dihydroxy-15beta,16beta-methyleneandrost-6-en-17-one;3????,5????-Dihydroxy-15????,16????-methylene-androst-6-en-17-one;3beta,5-Dihydroxy-15beta,16beta-methylen-5beta-androst-6-en-17-one;3I(2),5I(2)-Dihydroxy-15I(2),16I(2)-methylene-androst-6-en-17-one;(2S,4aR,4bS,6aS,7aS,8aS,8bS,10aR)-2,10a-Dihydroxy-4a,6a-dimethyl-2,3,4,4a,4b,5,6,6a,7a,8,8a,8b,8c,10a-tetradecahydrocyclopropa[4,5]cyclopenta[1,2-a]phenanthren-7(1H)-one

Chemical Property of 3 beta,5 beta-Dihydroxy-15 beta,16 beta-methylene-5 beta-androst-6-en-17-one

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 0.001Pa at 25℃
• Melting Point: 199-203 °C (dec.)
• Boiling Point: 467.26 °C at 760 mmHg
• PKA: 13.93±0.70(Predicted)
• Flash Point: 250.507 °C
• PSA: 57.53000
• Density: 1.259 g/cm³
• LogP: 2.70590
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 316.20384475
• Heavy Atom Count: 23
• Complexity: 612

Purity/Quality:

99% ^*data from raw suppliers

3beta,5beta-Dihydroxy-15alpha,16alpha-methylene-androst-6-en-17-one 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(CC1(C=CC3C2CCC4(C3C5CC5C4=O)C)O)O
• Isomeric SMILES: C[C@]12CC[C@@H](C[C@]1(C=C[C@@H]3[C@@H]2CC[C@]4([C@H]3[C@@H]5C[C@@H]5C4=O)C)O)O
• Uses: (3b,5b,15a,16a)-15,16-Dihydro-3,5-dihydroxy-3'H-cycloprop[15,16]androsta-6,15-dien-17-one is an impurity of the synthetic progestogen Drospirenone (D453200). It is used in the preparation of aldosterone antagonists.

Technology Process of 3 beta,5 beta-Dihydroxy-15 beta,16 beta-methylene-5 beta-androst-6-en-17-one

There total 1 articles about 3 beta,5 beta-Dihydroxy-15 beta,16 beta-methylene-5 beta-androst-6-en-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:

7β-hydroxy-15β,16β-methylene-3β-pivaloyloxy-5-androsten-17-one (82543-09-7) → 3β,5-dihydroxy-15β,16β-methylene-5β-androst-6-en-17-one (82543-15-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / tert-butylhydroperoxide, VO(C₅H₇O₂)2 / toluene / 2 h / 80 °C

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

3: 75 percent / Zn / acetic anhydride; tetrahydrofuran / 1.5 h / 70 °C

4: 94 percent / KOH, NaClO₄ / tetrahydrofuran; methanol / 2.5 h / Ambient temperature

With tert.-butylhydroperoxide; potassium hydroxide; VO(C₅H₇O₂)2; sodium perchlorate; triphenylphosphine; zinc; In tetrahydrofuran; pyridine; methanol; tetrachloromethane; dichloromethane; acetic anhydride; toluene;

Reference yield: 88.0%

diiodomethane (75-11-6) + 3β,5-dihydroxy-15β,16β-methylene-5β-androst-6-en-17-one (82543-15-5) → (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)

Guidance literature:

With copper; zinc; In 1,2-dimethoxyethane; at 55 ℃; for 5h;

Reference yield: 82.5%

propargyl alcohol (107-19-7) + 3β,5-dihydroxy-15β,16β-methylene-5β-androst-6-en-17-one (82543-15-5) → 17α-(3-hydroxypropynyl)-15β,16β-methylene-5β-androst-6-ene-3β,5,17β-triol (108674-97-1)

Guidance literature:

With potassium ethoxide; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1021/jm00391a023

upstream raw materials:

7β-hydroxy-15β,16β-methylene-3β-pivaloyloxy-5-androsten-17-one

Downstream raw materials:

(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

17α-(3-hydroxypropynyl)-15β,16β-methylene-5β-androst-6-ene-3β,5,17β-triol

15β,16β-methylene-3-oxo-17α-pregna-4,6-diene-21,17-carbolactone

Mespirenone

Refernces