(22E,24ξ)-4α,14α-Dimethyl-9β,19-cyclo-5α-stigmast-22-en-3β-ol

Base Information

• Chemical Name: (22E,24ξ)-4α,14α-Dimethyl-9β,19-cyclo-5α-stigmast-22-en-3β-ol
• CAS No.: 78330-50-4
• Molecular Formula: C₃₁H₅₂O
• Molecular Weight: 440.753
• Mol file: 78330-50-4.mol

Synonyms:(3S,4S,5S,8S,9S,10R,13R,14S,17R)-17-((E)-(1R,4S)-4-Ethyl-1,5-dimethyl-hex-2-enyl)-4,13,14-trimethyl-tetradecahydro-cyclopropa[9,10]cyclopenta[a]phenanthren-3-ol;

Chemical Property of (22E,24ξ)-4α,14α-Dimethyl-9β,19-cyclo-5α-stigmast-22-en-3β-ol

Chemical Property:

• PSA: 20.23000
• LogP: 8.27080

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (22E,24ξ)-4α,14α-Dimethyl-9β,19-cyclo-5α-stigmast-22-en-3β-ol

There total 12 articles about (22E,24ξ)-4α,14α-Dimethyl-9β,19-cyclo-5α-stigmast-22-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:

(R)-2-Isopropyl-5-[(3S,4S,10R,13R,14S,17R)-4,13,14-trimethyl-3-(tetrahydro-pyran-2-yloxy)-tetradecahydro-cyclopropa[9,10]cyclopenta[a]phenanthren-17-yl]-hexan-1-ol (78342-58-2) → cyclonervilol (78330-50-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 12 mg / pyridine / 0.5 h / Ambient temperature

2: 1.5 mg / NaHCO₃ / dimethylsulfoxide / 6 h / 178 °C

3: 6 mg / H₂ / PtO₂ / ethyl acetate; methanol / 48 h / Ambient temperature

4: 10 mg / pyridine / Ambient temperature

5: 5.2 mg / 5percent KOH / methanol / 1 h / Heating

With potassium hydroxide; hydrogen; sodium hydrogencarbonate; platinum(IV) oxide; In pyridine; methanol; dimethyl sulfoxide; ethyl acetate;

DOI:10.1248/cpb.33.1914

Reference yield:

(R)-5-((3S,4S,10R,13R,14S,17R)-3-Hydroxy-4,13,14-trimethyl-tetradecahydro-cyclopropa[9,10]cyclopenta[a]phenanthren-17-yl)-2-isopropyl-hexanoic acid (98263-85-5) → cyclonervilol (78330-50-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 20 mg / diethyl ether / Ambient temperature

2: 20 mg / CHCl₃ / 0.5 h / Ambient temperature

3: 14 mg / LiAlH₄ / diethyl ether / 5 h / Heating

4: 12 mg / pyridine / 0.5 h / Ambient temperature

5: 1.5 mg / NaHCO₃ / dimethylsulfoxide / 6 h / 178 °C

6: 6 mg / H₂ / PtO₂ / ethyl acetate; methanol / 48 h / Ambient temperature

7: 10 mg / pyridine / Ambient temperature

8: 5.2 mg / 5percent KOH / methanol / 1 h / Heating

With potassium hydroxide; lithium aluminium tetrahydride; hydrogen; sodium hydrogencarbonate; platinum(IV) oxide; In pyridine; methanol; diethyl ether; chloroform; dimethyl sulfoxide; ethyl acetate;

DOI:10.1248/cpb.33.1914

Reference yield:

(R)-5-((3S,4S,10R,13R,14S,17R)-3-Hydroxy-4,13,14-trimethyl-tetradecahydro-cyclopropa[9,10]cyclopenta[a]phenanthren-17-yl)-2-isopropyl-hexanoic acid methyl ester (78330-44-6) → cyclonervilol (78330-50-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 20 mg / CHCl₃ / 0.5 h / Ambient temperature

2: 14 mg / LiAlH₄ / diethyl ether / 5 h / Heating

3: 12 mg / pyridine / 0.5 h / Ambient temperature

4: 1.5 mg / NaHCO₃ / dimethylsulfoxide / 6 h / 178 °C

5: 6 mg / H₂ / PtO₂ / ethyl acetate; methanol / 48 h / Ambient temperature

6: 10 mg / pyridine / Ambient temperature

7: 5.2 mg / 5percent KOH / methanol / 1 h / Heating

With potassium hydroxide; lithium aluminium tetrahydride; hydrogen; sodium hydrogencarbonate; platinum(IV) oxide; In pyridine; methanol; diethyl ether; chloroform; dimethyl sulfoxide; ethyl acetate;

DOI:10.1248/cpb.33.1914

upstream raw materials:

cyclonervilol acetate

Acetic acid (3S,4S,10R,13R,14S,17R)-17-((E)-(1R,4S)-4-ethyl-1,5-dimethyl-hex-2-enyl)-4,13,14-trimethyl-tetradecahydro-cyclopropa[9,10]cyclopenta[a]phenanthren-3-yl ester

(R)-2-Isopropyl-5-[(3S,4S,10R,13R,14S,17R)-4,13,14-trimethyl-3-(tetrahydro-pyran-2-yloxy)-tetradecahydro-cyclopropa[9,10]cyclopenta[a]phenanthren-17-yl]-hexan-1-ol

(R)-5-((3S,4S,10R,13R,14S,17R)-3-Hydroxy-4,13,14-trimethyl-tetradecahydro-cyclopropa[9,10]cyclopenta[a]phenanthren-17-yl)-2-isopropyl-hexanoic acid

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.

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