(16α-bromine)-3α-Dehydroepiandrosterone

Base Information

• Chemical Name: (16α-bromine)-3α-Dehydroepiandrosterone
• CAS No.: 1093-91-0
• Molecular Formula: C19H27 Br O2
• Molecular Weight: 367.32048
• Mol file: 1093-91-0.mol

Synonyms:Androst-5-en-17-one,16a-bromo-3b-hydroxy- (6CI,7CI,8CI); 16a-Bromo-3b-hydroxy-5-androsten-17-one;16a-Bromodehydroepiandrosterone; 5-Androsten-16a-bromo-3b-ol-17-one

Chemical Property of (16α-bromine)-3α-Dehydroepiandrosterone

Chemical Property:

• PSA: 37.30000
• LogP: 4.25260

Purity/Quality:

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

16a-Bromodehydro epiandrosterone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Intermediate in the preparation of Testosterone and related derivatives.

Technology Process of (16α-bromine)-3α-Dehydroepiandrosterone

There total 9 articles about (16α-bromine)-3α-Dehydroepiandrosterone 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: 98.0%

dehydroepiandrosterone (53-43-0) → 3β-hydroxy-16α-bromoandrost-5-ene-17-one (1093-91-0,158342-64-4)

Guidance literature:

With copper(ll) bromide; In methanol; for 12h; Heating;

DOI:10.1021/jo00142a004

Reference yield: 91.0%

prasterone acetate (853-23-6) → 3β-hydroxy-16α-bromoandrost-5-ene-17-one (1093-91-0,158342-64-4)

Guidance literature:

With copper(ll) bromide; In methanol; for 8h; Heating;

DOI:10.1002/anie.200454237

Reference yield: 82.0%

dehydroepiandrosterone (53-43-0,571-35-7,2283-82-1,24357-33-3,25375-38-6,102340-20-5) → 3β-Hydroxy-16α-brom-androst-5-en-17-on (1093-91-0,55821-49-3,74644-60-3,151434-12-7,158342-64-4)

Guidance literature:

With copper(ll) bromide; In methanol; for 8h; Reflux;

DOI:10.1016/j.steroids.2016.05.004

upstream raw materials:

dehydroepiandrosterone

3β-acetoxy-16α-bromoandrost-5-en-17-one

dehydroepiandrosterone

16β-bromo-3β-hydroxy-5-androsten-17-one

Downstream raw materials:

3β,17β-dihydroxyandrost-5-en-16-one

16α-hydroxy dehydroepiandrosterone

16β-bromo-3β-hydroxy-5-androsten-17-one

(R)-3,17-Dihydroxy-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,17-tetradecahydro-cyclopenta[a]phenanthren-16-one

Refernces

• 1、 Cantineau, R.,Kremers, P.,Graeve, J. De,Cornelis, A.,Laszlo, P.,et al.. "SYNTHESIS OF 16α-3H ANDROGEN AND ESTROGEN SUBSTRATES FOR 16α-HYDROXYLASE". . p. 177 - 194. Retrieved 1981.
• 2、 Zhao, Jian-Wei,Wu, Zeng-Hui,Guo, Jia-Wen,Huang, Ming-Jie,You, Ya-Zhen,Liu, Hong-Min,Huang, Li-Hua. "Synthesis and anti-gastric cancer activity evaluation of novel triazole nucleobase analogues containing steroidal/coumarin/quinoline moieties". . . Retrieved 2019.
• 3、 Numazawa, Mitsuteru,Osawa, Yoshio. "Controlled Alkaline Hydrolysis of 16-Bromo-17-keto Steroids without Ketol Rearrangement and Its Reaction Mechanism". . p. 5402 - 5404. Retrieved 1980.
• 4、 Hamilton, Niall M.,Dawson, Martin,Fairweather, Emma E.,Hamilton, Nicola S.,Hitchin, James R.,James, Dominic I.,Jones, Stuart D.,Jordan, Allan M.,Lyons, Amanda J.,Small, Helen F.,Thomson, Graeme J.,Waddell, Ian D.,Ogilvie, Donald J.. "Novel steroid inhibitors of glucose 6-phosphate dehydrogenase". supporting information; experimental part. p. 4431 - 4445. Retrieved 2012/09/11.