(20S)-4,4,14-Trimethyl-20-(dimethylamino)-9β,19-cyclo-5α-pregnan-3-one

Base Information

• Chemical Name: (20S)-4,4,14-Trimethyl-20-(dimethylamino)-9β,19-cyclo-5α-pregnan-3-one
• CAS No.: 17934-61-1
• Molecular Formula: C26H43NO
• Molecular Weight: 385.63
• Mol file: 17934-61-1.mol

Synonyms:(5R,8S,9S,10R,13R,14S,17S)-17-((S)-1-Dimethylamino-ethyl)-4,4,13,14-tetramethyl-tetradecahydro-cyclopropa[9,10]cyclopenta[a]phenanthren-3-one;

Chemical Property of (20S)-4,4,14-Trimethyl-20-(dimethylamino)-9β,19-cyclo-5α-pregnan-3-one

Chemical Property:

• Melting Point: 157-159 °C
• Boiling Point: 463.6±18.0 °C(Predicted)
• PKA: 9.60±0.50(Predicted)
• PSA: 20.31000
• Density: 1.04±0.1 g/cm3(Predicted)
• LogP: 5.94470

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (20S)-4,4,14-Trimethyl-20-(dimethylamino)-9β,19-cyclo-5α-pregnan-3-one

There total 6 articles about (20S)-4,4,14-Trimethyl-20-(dimethylamino)-9β,19-cyclo-5α-pregnan-3-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:

cyclobuxoviridine L (10088-20-7) → Buxandonin (17934-61-1)

Guidance literature:

With hydrogen; platinum(IV) oxide; In ethanol;

DOI:10.1039/j39660001412

Reference yield:

Acetic acid (3S,5R,8S,9S,10R,13R,14S,17S)-4,4,13,14-tetramethyl-17-[(R)-1-(toluene-4-sulfonyloxy)-ethyl]-tetradecahydro-cyclopropa[9,10]cyclopenta[a]phenanthren-3-yl ester (64492-99-5) → Buxandonin (17934-61-1)

Guidance literature:

Multi-step reaction with 3 steps

1: NaN₃ / hexamethylphosphoric acid triamide

2: (i) LiAlH₄, (ii) /BRN= 1209228/, aq. HCO₂H

3: CrO₃, aq. H₂SO₄

With chromium(VI) oxide; sodium azide; sulfuric acid; In N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1016/0040-4020(77)80224-X

Reference yield:

(3S,5R,8S,9S,10R,13R,14S,17S)-17-((S)-1-Dimethylamino-ethyl)-4,4,13,14-tetramethyl-tetradecahydro-cyclopropa[9,10]cyclopenta[a]phenanthren-3-ol (7759-48-0) → Buxandonin (17934-61-1)

Guidance literature:

With chromium(VI) oxide; sulfuric acid;

DOI:10.1016/0040-4020(77)80224-X

upstream raw materials:

cyclobuxoviridine L

(3S,5R,8S,9S,10R,13R,14S,17S)-17-((S)-1-Dimethylamino-ethyl)-4,4,13,14-tetramethyl-tetradecahydro-cyclopropa[9,10]cyclopenta[a]phenanthren-3-ol

Acetic acid (3S,5R,8S,9S,10R,13R,14S,17S)-4,4,13,14-tetramethyl-17-[(R)-1-(toluene-4-sulfonyloxy)-ethyl]-tetradecahydro-cyclopropa[9,10]cyclopenta[a]phenanthren-3-yl ester

Acetic acid (3S,5R,8S,9S,10R,13R,14S,17S)-17-((S)-1-azido-ethyl)-4,4,13,14-tetramethyl-tetradecahydro-cyclopropa[9,10]cyclopenta[a]phenanthren-3-yl ester

Refernces

• 1、 Khuong-Huu,Magdeleine. "Steroidal alkaloids XCVI. Buxaceae family (13th communication). Alkaloids of Buxus malayana Ridl.: cycloprotobuxine C, cyclovirobuxine C, N-formyl cyclovirobuxine B, O-vanillyl cyclovirobuxine B, cyclobuxophylline M". . p. 211 - 222. Retrieved 2007/10/15.