4α,14α,28-Trimethyl-9β,19-cyclo-5α-stigmast-25-en-3β-ol

Base Information

• Chemical Name: 4α,14α,28-Trimethyl-9β,19-cyclo-5α-stigmast-25-en-3β-ol
• CAS No.: 78330-51-5
• Molecular Formula: C₃₂H₅₄O
• Molecular Weight: 454.78
• Mol file: 78330-51-5.mol

Synonyms:(3S,4S,5S,8S,9S,10R,13R,14S)-17-((1R,4R)-4-Isopropyl-1,5-dimethyl-hex-5-enyl)-4,13,14-trimethyl-tetradecahydro-cyclopropa[9,10]cyclopenta[a]phenanthren-3-ol;

Chemical Property of 4α,14α,28-Trimethyl-9β,19-cyclo-5α-stigmast-25-en-3β-ol

Chemical Property:

• PSA: 20.23000
• LogP: 8.66090

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4α,14α,28-Trimethyl-9β,19-cyclo-5α-stigmast-25-en-3β-ol

There total 2 articles about 4α,14α,28-Trimethyl-9β,19-cyclo-5α-stigmast-25-en-3β-ol 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:

Acetic acid (3S,4S,10R,13R,14S,17R)-17-((R)-4-isopropyl-1,5-dimethyl-hex-5-enyl)-4,13,14-trimethyl-tetradecahydro-cyclopropa[9,10]cyclopenta[a]phenanthren-3-yl ester (78342-57-1) → cyclohomonervilol (78330-51-5)

Guidance literature:

With potassium hydroxide; In methanol; for 1h; Heating;

DOI:10.1248/cpb.33.1914

Reference yield:

cyclohomonervilol acetate (78342-57-1) → cyclohomonervilol (78330-51-5)

Guidance literature:

With Alkaline;

DOI:10.1016/0040-4039(81)80127-X

Reference yield:

cyclohomonervilol (78330-51-5) → 24S-dihydrocyclofuntumienol benzoate (98155-98-7,98302-98-8,98303-02-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 5 mg / pyridine / Ambient temperature

2: 5.5 mg / osmium tetroxide / Ambient temperature

3: 1) HIO₄, 2) NaBH₄ / 1) dioxane-water, 8 min, ice-cooling; 2) MeOH, 30 min

4: 3.5 mg / pyridine / 12 h / Ambient temperature

5: 0.01 mg / tributyltin hydride / toluene / 4 h / 130 °C

6: H₂/PtO₂

With pyridine; platinum(IV) oxide; sodium tetrahydroborate; osmium(VIII) oxide; hydrogen; tri-n-butyl-tin hydride; periodic acid; In pyridine; toluene;

upstream raw materials:

cyclohomonervilol acetate

Acetic acid (3S,4S,10R,13R,14S,17R)-17-((R)-4-isopropyl-1,5-dimethyl-hex-5-enyl)-4,13,14-trimethyl-tetradecahydro-cyclopropa[9,10]cyclopenta[a]phenanthren-3-yl ester

Downstream raw materials:

cyclohomonervilol benzoate

Benzoic acid (3S,4S,5S,8S,9S,10R,13R,14S)-17-((1R,4R)-4-isopropyl-1-methyl-5-phenoxythiocarbonyloxy-hexyl)-4,13,14-trimethyl-tetradecahydro-cyclopropa[9,10]cyclopenta[a]phenanthren-3-yl ester

cyclofuntumienol benzoate

24S-dihydrocyclofuntumienol benzoate

Refernces

• 1、 Kikuchi,Kadota,Suehara,Namba. "New triterpenes from Nervilia purpurea Schlechter, an orchidaceous plant structure of cyclonervilol and cyclohomonervilol and chemical correlation with cycloeucalenol". . p. 465 - 468. Retrieved 2007/10/02.