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:

99% ^*data from raw suppliers

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:

cycloeucalenol acetate

cycloeucalenol

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

Refernces

New triterpenes from Nervilia purpurea Schlechter, an orchidaceous plant structure of cyclonervilol and cyclohomonervilol and chemical correlation with cycloeucalenol

10.1016/0040-4039(81)80127-X

The research aimed to isolate and identify new triterpenes from Nervilia purpurea Schlechter, an orchidaceous plant used in folk medicine for treating wounds and hypertension in Formosa. The study successfully isolated two new triterpenes, cyclonervilol and cyclohomonervilol, and proposed their respective structures based on chemical and spectroscopic evidence. The chemicals used in the process included ether for extraction, silica gel for chromatography with CH2Cl2-hexane, and various reagents for acetylation, such as AgNO3-SiO2 for chromatography, benzene-hexane for elution, and osmium tetroxide and HI04 for oxidation. The study also involved the use of alkaline hydrolysis to obtain the free triterpenes from their acetate derivatives, and other chemicals like NaOD in MeOD for deuteration, Eu(DPM13 for NMR analysis, and Pb(OAc)4 for oxidation to carboxylic acids. The research concluded that the structures of the new triterpenes were established, with the exception of the stereochemistry at the C-24 position, and confirmed their chemical correlation with cycloeucalenol.