19-Hydroxycholest-5-en-3-yl acetate

Base Information

• Chemical Name: 19-Hydroxycholest-5-en-3-yl acetate
• CAS No.: 750-59-4
• Molecular Formula: C29H48 O3
• Molecular Weight: 444.698
• NSC Number: 123342
• DSSTox Substance ID: DTXSID20996496
• Mol file: 750-59-4.mol

Synonyms:19-Hydroxycholest-5-en-3-yl acetate;[10-(hydroxymethyl)-13-methyl-17-(6-methylheptan-2-yl)-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate;750-59-4;19-Hydroxycholesteryl acetate;DTXSID20996496;Cholest-5-ene-3.beta., 3-acetate;NSC123342;NSC-123342;Cholest-5-ene-3, 3-acetate, (3.beta.)-;FT-0669472

Chemical Property of 19-Hydroxycholest-5-en-3-yl acetate

Chemical Property:

• Vapor Pressure: 1.93E-13mmHg at 25°C
• Melting Point: 121-123?C
• Boiling Point: 529.9°C at 760 mmHg
• Flash Point: 195.4°C
• PSA: 46.53000
• Density: 1.04g/cm³
• LogP: 6.93190
• Storage Temp.: −20°C
• Solubility.: Chloroform, Methanol
• XLogP3: 7.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 444.36034539
• Heavy Atom Count: 32
• Complexity: 711

Purity/Quality:

97% ^*data from raw suppliers

19-HydroxyCholesteryl3-Acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)OC(=O)C)CO)C
• Uses: A C-19 functionalized cholesterol derivative and popular substrate for steroid biotransformations.

Technology Process of 19-Hydroxycholest-5-en-3-yl acetate

There total 14 articles about 19-Hydroxycholest-5-en-3-yl acetate 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: 89.0%

(3S,5R,6R,8S,9S,10R,13R,14S,17R)-5-bromo-13-methyl-17-((R)-6-methylheptan-2-yl)hexadecahydro-6,10-(epoxymethano)cyclopenta[a]phenanthren-3-yl acetate (1258-07-7) → 3β-acetoxycholest-5-en-19-ol (750-59-4)

Guidance literature:

With water; acetic acid; zinc; at 20 ℃; for 75h;

DOI:10.1016/j.tetlet.2016.07.067

Reference yield: 74.0%

(3S,5R,6R,8S,9S,10R,13R,14S,17R)-5-bromo-13-methyl-17-((R)-6-methylheptan-2-yl)hexadecahydro-6,10-(epoxymethano)cyclopenta[a]phenanthren-3-yl acetate (1258-07-7) → 3β-acetoxycholest-5-en-19-ol (750-59-4) + Acetic acid (3S,5R,6S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-20-oxa-cyclopropa[5,6]cyclopenta[a]phenanthren-3-yl ester (1256-31-1,2953-35-7,4092-57-3,14456-17-8,55400-50-5,68974-60-7,68974-61-8)

Guidance literature:

With zinc; In ethanol; Heating;

DOI:10.1016/S0009-3084(99)00005-5

Reference yield:

Cholesteryl acetate (604-35-3) → 3β-acetoxycholest-5-en-19-ol (750-59-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 65 percent / NBS, 60percent HClO₄ / diethyl ether; H₂O / 3 h / Ambient temperature

2: 97 percent / Pb(OAc)4, CaCO₃, I₂ / cyclohexane / 1 h / Heating; Irradiation

3: 79 percent / Zn, CuCl / ethanol / 10 h / Heating

With lead(IV) acetate; N-Bromosuccinimide; perchloric acid; iodine; calcium carbonate; copper(l) chloride; zinc; In diethyl ether; ethanol; cyclohexane; water;

upstream raw materials:

(3S,5R,6R,8S,9S,10R,13R,14S,17R)-5-bromo-13-methyl-17-((R)-6-methylheptan-2-yl)hexadecahydro-6,10-(epoxymethano)cyclopenta[a]phenanthren-3-yl acetate

cholesterol

Cholesteryl acetate

(3S,5R,6R,8S,9S,10R,13R,14S,17R)-5-bromo-6-hydroxy-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate

Downstream raw materials:

6β,19-epoxy-5-(phenylselenenyl)-5α-cholestan-3β-yl acetate

5-Cholesten-3β,19-diol-3-acetat-19-benzoat

3β,19-diacetoxycholest-Δ⁵-ene

(3S,8S,9S,10S,13R,14S,17R)-13-methyl-17-((R)-6-methylheptan-2-yl)-10-((tosyloxy)methyl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate

Refernces

• 1、 Taspinar, ?mer,Wilczek, Tobias,Erver, Julian,Breugst, Martin,Neud?rfl, J?rg-Martin,Schmalz, Hans-Günther. "Synthesis of the 8,19-Epoxysteroid Eurysterol A". supporting information. p. 4256 - 4260. Retrieved 2020/03/23.
• 2、 Oikawa, Yuya,Uchiyama, Daiki,Shirasawa, Takuya,Oikawa, Masato,Ishikawa, Yuichi. "Synthetic study of strongylophorines: stereoselective construction of the characteristic lactone bridge". supporting information. p. 3949 - 3951. Retrieved 2016/08/09.