3alpha-Hydroxy-5beta-pregnan-20-one ethylene acetal

Base Information

• Chemical Name: 3alpha-Hydroxy-5beta-pregnan-20-one ethylene acetal
• CAS No.: 18000-89-0
• Molecular Formula: C₂₃H₃₈O₃
• Molecular Weight: 362.553
• NSC Number: 85996
• Nikkaji Number: J322.220I
• ChEMBL ID: CHEMBL3137803
• Mol file: 18000-89-0.mol

Synonyms:NSC85996;CHEMBL3137803;NSC-85996;18000-89-0

Chemical Property of 3alpha-Hydroxy-5beta-pregnan-20-one ethylene acetal

Chemical Property:

• Vapor Pressure: 2.92E-10mmHg at 25°C
• Refractive Index: 1.529
• Boiling Point: 456.7 °C at 760 mmHg
• Flash Point: 230 °C
• Density: 1.085 g/cm³
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 362.28209507
• Heavy Atom Count: 26
• Complexity: 556

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(CC1CCC3C2CCC4(C3CCC4C5(OCCO5)C)C)O
• Isomeric SMILES: C[C@]12CC[C@H](C[C@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@H]4C5(OCCO5)C)C)O

Technology Process of 3alpha-Hydroxy-5beta-pregnan-20-one ethylene acetal

There total 8 articles about 3alpha-Hydroxy-5beta-pregnan-20-one ethylene acetal 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: 100.0%

isopregnanolone (516-55-2) + ethylene glycol (107-21-1) → (3β,5α)-3-hydroxypregnan-20-one 1,2-ethanediyl acetal (2124-26-7,14615-04-4,14957-69-8,18000-89-0,18125-29-6,95670-99-8,126451-96-5)

Guidance literature:

With toluene-4-sulfonic acid; trimethyl orthoformate; In dichloromethane; at 20 ℃;

DOI:10.1021/jm300317k

Reference yield:

Pregnenolone (145-13-1) → (3β,5α)-3-hydroxypregnan-20-one 1,2-ethanediyl acetal (2124-26-7,14615-04-4,14957-69-8,18000-89-0,18125-29-6,95670-99-8,126451-96-5)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium 10% on activated carbon; hydrogen / ethanol / 5 h / Inert atmosphere

2: toluene-4-sulfonic acid; trimethyl orthoformate / dichloromethane / 20 °C

With palladium 10% on activated carbon; hydrogen; toluene-4-sulfonic acid; trimethyl orthoformate; In ethanol; dichloromethane;

DOI:10.1021/jm300317k

Reference yield:

5β-pregnane-3,20-dione cyclic 20-(1,2-ethanediyl acetal) (1452-23-9,14957-70-1,18000-86-7,101311-20-0,101311-21-1) → 3α-Hydroxy-20-ethylendioxy-5β-pregnan (18000-89-0)

Guidance literature:

With lithium aluminium tetrahydride; diethyl ether; benzene;

upstream raw materials:

isopregnanolone

ethylene glycol

Pregnenolone

5β-pregnane-3,20-dione cyclic 20-(1,2-ethanediyl acetal)

Downstream raw materials:

(3α,5α)-3-aminopregnan-20-one

(3β,5α)-3-aminopregnan-20-one

(3α,5α)-3-aminopregnan-20-one hydrochloride

N-[(3β,5α)-20-oxopregnan-3-yl]benzenesulfonamide

Refernces

• 1、 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.