2,3-Seco-5-androstan-17-one-2,3-dicarboxylic acid

Base Information

• Chemical Name: 2,3-Seco-5-androstan-17-one-2,3-dicarboxylic acid
• CAS No.: 1165-38-4
• Molecular Formula: C₁₉H₂₈O₅
• Molecular Weight: 336.428
• Mol file: 1165-38-4.mol

Synonyms:1H-Benz[e]indene-6,7-diaceticacid, dodecahydro-3a,6-dimethyl-3-oxo-, [3aS-(3aa,5ab,6b,7a,9aa,9bb)]-; 2,3-Seco-5a-androstane-2,3-dioic acid,17-oxo- (6CI,7CI,8CI); 1H-Benz[e]indene-6,7-diacetic acid,dodecahydro-3a,6-dimethyl-3-oxo-, stereoisomer; 17-Oxo-2,3-seco-5a-androstane-2,3-dioic acid; NSC148935

Chemical Property of 2,3-Seco-5-androstan-17-one-2,3-dicarboxylic acid

Chemical Property:

• Vapor Pressure: 5.71E-13mmHg at 25°C
• Refractive Index: 1.52
• Boiling Point: 537.2°Cat760mmHg
• Flash Point: 292.8°C
• PSA: 91.67000
• Density: 1.173g/cm³
• LogP: 3.36370

Purity/Quality:

98%,99%, ^*data from raw suppliers

2,3-SECO-5-ALPHA-ANDROSTANE-17-ONE-2,3-DIOIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2,3-Seco-5-androstan-17-one-2,3-dicarboxylic acid

There total 7 articles about 2,3-Seco-5-androstan-17-one-2,3-dicarboxylic acid 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: 83.7%

Epiandrosterone (481-29-8) → 17-Oxo-2.3-seco-5α-androstan-2.3-dicarbonsaeure (1165-38-4)

Guidance literature:

With chromium(VI) oxide; sulfuric acid; acetic acid; In water; for 2h; Product distribution / selectivity; Cooling with ice;

Reference yield:

17-Oxo-3-acetyl-5α-androsten-(2) (17006-92-7) → 17-Oxo-2.3-seco-5α-androstan-2.3-dicarbonsaeure (1165-38-4)

Guidance literature:

With potassium permanganate; In acetone;

Reference yield:

(3S,5S,8R,9S,10S,13S,14S,17S)-3-ethynyl-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol (10148-98-8) → 17-Oxo-2.3-seco-5α-androstan-2.3-dicarbonsaeure (1165-38-4)

Guidance literature:

Multi-step reaction with 3 steps

1: (i) aq. HCO₂H, (ii) NaOH, MeOH

2: CrO₃, aq. H₂SO₄ / acetone

3: KMnO₄ / acetone

With chromium(VI) oxide; potassium permanganate; sulfuric acid; In acetone;

upstream raw materials:

((3S,5S,8R,9S,10S,13S,14S,17S)-3,17-Diacetoxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl)-oxo-acetic acid methyl ester

17-Oxo-3-acetyl-5α-androsten-(2)

Epiandrosterone

(3S,5S,8R,9S,10S,13S,14S,17S)-3-ethynyl-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol

Refernces

• 1、 -. "CYP11B, CYP17, AND/OR CYP21 INHIBITORS". Page/Page column 206. . Retrieved 2012/06/30.
• 2、 Gupta,Jones,Caspi. "Preparation and transformations of steroidal butadiynes". . p. 1420 - 1427. Retrieved 2007/10/09.