(10,13-Dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl) 4-methylbenzenesulfonate

Base Information

• Chemical Name: (10,13-Dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl) 4-methylbenzenesulfonate
• CAS No.: 10429-07-9
• Molecular Formula: C₂₆H₃₆O₄S
• Molecular Weight: 444.635
• European Community (EC) Number: 600-553-3
• Mol file: 10429-07-9.mol

Synonyms:androsterone tosylate;(10,13-dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl) 4-methylbenzenesulfonate;AKOS004900535

Chemical Property of (10,13-Dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl) 4-methylbenzenesulfonate

Chemical Property:

• Density: 1.18g/cm3 at 25℃
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 444.23343080
• Heavy Atom Count: 31
• Complexity: 808

Purity/Quality:

99.9% ^*data from raw suppliers

3β-(4-Methylphenylsulfonyloxy)-5α-androstan-17-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OC2CCC3(C(C2)CCC4C3CCC5(C4CCC5=O)C)C
• Uses: 3β-(4-Methylphenylsulfonyloxy)-5α-androstan-17-one is an important reagent in the synthesis of aminosteroids and rocuronium bromide intermediate. Rocuronium bromide is an amino steroid non-depolarizing neuro muscular blocker. Also functions as a reagent in the preparation of androstanes as antiarrhythmics.

Technology Process of (10,13-Dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl) 4-methylbenzenesulfonate

There total 6 articles about (10,13-Dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl) 4-methylbenzenesulfonate 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: 92.0%

Epiandrosterone (481-29-8) + p-toluenesulfonyl chloride (98-59-9) → 3β-tosyloxy-5α-androstan-17-one (10429-07-9)

Guidance literature:

With pyridine; at 20 ℃; for 20h;

DOI:10.1016/j.steroids.2021.108928

Reference yield:

dehydroepiandrosterone (53-43-0) → 3β-tosyloxy-5α-androstan-17-one (10429-07-9)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen; palladium 10% on activated carbon / ethanol / 12 h / 40 °C / 2068.65 Torr

2: pyridine / 6 h / 40 °C

With pyridine; palladium 10% on activated carbon; hydrogen; In ethanol;

Reference yield:

→ 3α-p-Toluolsulfonyloxy-5α-androstan-17-on (5226-16-4,5599-99-5,10429-00-2,10429-07-9,24174-19-4,136032-10-5)

Guidance literature:

Alkohol, Tosylchlorid;

DOI:10.1021/jo01281a034

upstream raw materials:

Epiandrosterone

p-toluenesulfonyl chloride

dehydroepiandrosterone

Downstream raw materials:

androsterone acetate

cis-androsterone

5α-androst-2-en-17-one

3α-Formoxy-5α-androstan-17-on

Refernces

• 1、 Ciceri, Samuele,Colombo, Diego,Ferraboschi, Patrizia,Grisenti, Paride,Iannone, Marco,Mori, Matteo,Meneghetti, Fiorella. "Vecuronium bromide and its advanced intermediates: A crystallographic and spectroscopic study". . . Retrieved 2021/10/25.
• 2、 Liu, Chenjing,Chen, Dengfeng,Fu, Yuanyuan,Wang, Fei,Luo, Jinyue,Huang, Shenlin. "Sulfoxide Reduction/C(sp3)-S Metathesis Cascade in Ionic Liquid". supporting information. p. 5701 - 5705. Retrieved 2020/07/24.