3β-(Acetoxy)-5α-cholest-5-en-24-one

Base Information

• Chemical Name: 3β-(Acetoxy)-5α-cholest-5-en-24-one
• CAS No.: 20981-59-3
• Molecular Formula: C29H46O3
• Molecular Weight: 442.682
• Mol file: 20981-59-3.mol

Synonyms:3β-(Acetoxy)-5α-cholest-5-en-24-one;3β-Acetoxycholest-5-en-24-one

Chemical Property of 3β-(Acetoxy)-5α-cholest-5-en-24-one

Chemical Property:

• PSA: 43.37000
• LogP: 7.13850

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3β-(Acetoxy)-5α-cholest-5-en-24-one

There total 2 articles about 3β-(Acetoxy)-5α-cholest-5-en-24-one 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: 5.9%

Cholesteryl acetate (604-35-3) → Pregnenolone acetate (1778-02-5) + 7-ketocholesteryl acetate (809-51-8) + 3β-acetoxy-cholest-5-en-24-one (20981-59-3) + Acetic acid (3S,8R,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-15-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester (108354-96-7)

Guidance literature:

With pyridine; oxygen; acetic acid; zinc; iron; In water; for 5h; Further byproducts given; Ambient temperature; Gif system;

Reference yield: 5.9%

Cholesteryl acetate (604-35-3) → Pregnenolone acetate (1778-02-5) + 7-ketocholesteryl acetate (809-51-8) + 3β-acetoxy-cholest-5-en-24-one (20981-59-3) + Acetic acid (3S,8S,9S,10R,13S,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-16-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester (5888-06-2)

Guidance literature:

With pyridine; oxygen; acetic acid; zinc; iron; In water; for 5h; Further byproducts given; Ambient temperature; Gif system;

Reference yield:

3β-acetoxy-cholest-5-en-24-one (20981-59-3) → (5R,7R,8R,9S,10S,13R,14S,17R)-17-[(R)-4-(tert-Butyl-dimethyl-silanyloxy)-1,5-dimethyl-hexyl]-7-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-one O-benzyl-oxime (159790-99-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 80 percent / sodium borohydride, calcium chloride / tetrahydrofuran / 5 h / Ambient temperature

2: 90 percent / imidazole / CH₂Cl₂ / 16 h / Ambient temperature

3: 46 percent / chromium hexacarbonyl, tert-butyl hydroperoxide / acetonitrile / 12 h / Heating

4: 81 percent / Li, liq. NH₃ / diethyl ether / 0.17 h / -78 °C

5: 80 percent / K-selectride / tetrahydrofuran / 5 h / -50 °C

6: 88 percent / NaCN / methanol / 8 h / Heating

7: 59 percent / aluminum tri-tert-butoxide, cyclohexanone / toluene / 20 h / 120 °C

8: 97 percent / C₅H₅N / ethanol / 16 h / Heating

With pyridine; 1H-imidazole; tert.-butylhydroperoxide; sodium tetrahydroborate; sodium cyanide; ammonia; cyclohexanone; lithium; aluminum tri-tert-butoxide; potassium tri-sec-butyl-borohydride; chromium⁽⁰⁾ hexacarbonyl; calcium chloride; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; toluene; acetonitrile;

DOI:10.1016/0040-4039(94)88254-1

upstream raw materials:

Cholesteryl acetate

Downstream raw materials:

24(S)-hydroxycholesterol

24(R)-Hydroxycholesterol

24-methylene cholesterol

(5R,7R,8R,9S,10S,13R,14S,17R)-17-[(R)-4-(tert-Butyl-dimethyl-silanyloxy)-1,5-dimethyl-hexyl]-7-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-one O-benzyl-oxime

Refernces