Epifriedelal acetate

Base Information

• Chemical Name: Epifriedelal acetate
• CAS No.: 2259-07-6
• Molecular Formula: C32H54O2
• Molecular Weight: 470.77
• Mol file: 2259-07-6.mol

Synonyms:Epifriedelal acetate;24,25,26-Trinoroleanan-3-ol, 5,9,13-trimethyl-, acetate, (3β,4β,5β,8α,9β,10α,13α,14β)-

Chemical Property of Epifriedelal acetate

Chemical Property:

• PSA: 26.30000
• LogP: 8.81960

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Epifriedelal acetate

There total 20 articles about Epifriedelal 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: 54.0%

epifriedelanol (5085-72-3,7506-18-5,16844-71-6,105370-95-4) + 2-O-acetyl-3,4,6-tri-O-benzyl-D-glucopyranosyl trichloroacetimidate (189182-66-9) → 3β-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)friedelanol (524041-25-6) + 3β-acetoxy-friedelane (2259-07-6)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1002/ejoc.200500816

Reference yield: 30.0%

epifriedelanol (5085-72-3,7506-18-5,16844-71-6,105370-95-4) + acetic anhydride (108-24-7) → 3β-acetoxy-friedelane (2259-07-6) + friedel-2-ene (53013-35-7)

Guidance literature:

epifriedelanol; acetic anhydride; With boron trifluoride diethyl etherate; In chloroform; at 20 ℃; for 24h;

With water; sodium acetate; In chloroform; for 0.5h; Reflux;

DOI:10.1039/c8nj00009c

Reference yield:

(3S,4R,4aS,6aS,6bR,8aS,12aS,12bS,14aS,14bS)-4,4a,6b,8a,11,11,12b,14a-Octamethyl-docosahydro-picene-3,8-diol (33465-90-6,73255-45-5,79862-12-7) → 3β-acetoxy-friedelane (2259-07-6)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / Ambient temperature

2: 288 mg / 5percent KOH / methanol / 6 h / 50 °C

3: 8 mg / methanesulfonyl chloride / pyridine / 48 h / Ambient temperature

4: 1 mg / hydrogen, charcoal / Pd-C / ethyl acetate / 24 h / Ambient temperature

With potassium hydroxide; hydrogen; pyrographite; methanesulfonyl chloride; palladium on activated charcoal; In pyridine; methanol; ethyl acetate;

DOI:10.1248/cpb.29.1819

upstream raw materials:

pyridine

epifriedelanol

acetic anhydride

Acetic acid (3S,4R,4aS,6aS,6bR,8aR,12aR,12bS,14aS,14bS)-4,4a,6b,8a,11,11,12b,14a-octamethyl-1,2,3,4,4a,5,6,6a,6b,8a,9,10,11,12,12a,12b,13,14,14a,14b-icosahydro-picen-3-yl ester

Refernces

• 1、 Schimmel, Joerg,Eleuterio, M. Ines Passos,Ritter, Gerd,Schmidt, Richard R.. "Synthesis of saponins with cholestanol, cholesterol, and friedelanol as aglycones". . p. 1701 - 1721. Retrieved 2007/10/03.
• 2、 Kikuchi,Niwa,Yokoi,Kadota. "Studies on the neutral constituents of Pachysandra terminalis Sieb. et Zucc. VIII. Methyl migration in the dehydration reaction of pachysonol and pachysandiol-B derivatives". . p. 1819 - 1826. Retrieved 2007/10/02.