(2S)-2-[(3S,8S,9S,10R,13S,14S,17R)-3-acetyloxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]propanoic acid

Base Information

• Chemical Name: (2S)-2-[(3S,8S,9S,10R,13S,14S,17R)-3-acetyloxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]propanoic acid
• CAS No.: 1474-14-2
• Molecular Formula: C24H36 O4
• Molecular Weight: 388.547
• Nikkaji Number: J468.336F
• Mol file: 1474-14-2.mol

Synonyms:1474-14-2;(2S)-2-[(3S,8S,9S,10R,13S,14S,17R)-3-acetyloxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]propanoic acid;Pregn-5-ene-20-carboxylic acid, 3-(acetyloxy)-, (3beta,20S)-(9CI);NSC 224321;23,24-Bisnor-3beta-acetoxy-5beta-cholen-22-oic acid;SCHEMBL10705970;(20S)-3beta-acetoxy-5-pregnene-20-carboxylic acid;22,23-Bisnor-5-cholenic acid, 3.beta.-hydroxy, acetate(ester);Pregn-5-ene-20-carboxylic acid, 3-(acetyloxy)-, (3beta,20S)-

Chemical Property of (2S)-2-[(3S,8S,9S,10R,13S,14S,17R)-3-acetyloxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]propanoic acid

Chemical Property:

• Vapor Pressure: 1.21E-11mmHg at 25°C
• Boiling Point: 506.8°Cat760mmHg
• Flash Point: 166.4°C
• Density: 1.13g/cm³
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 388.26135963
• Heavy Atom Count: 28
• Complexity: 697

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)OC(=O)C)C)C)C(=O)O
• Isomeric SMILES: C[C@@H]([C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)OC(=O)C)C)C)C(=O)O

Technology Process of (2S)-2-[(3S,8S,9S,10R,13S,14S,17R)-3-acetyloxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]propanoic acid

There total 33 articles about (2S)-2-[(3S,8S,9S,10R,13S,14S,17R)-3-acetyloxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]propanoic acid 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: 91.0%

(20S)-3β-acetoxybisnorchol-5-en-22-al (10211-88-8) → 3β-acetoxybisnor-5-cholenic acid (1474-14-2)

Guidance literature:

With sodium chlorite; dipotassium hydrogenphosphate; In tetrahydrofuran; water; tert-butyl alcohol; at 0 - 20 ℃;

Reference yield:

5α,6β-dibromostigmastan-3β-yl acetate (32212-73-0) → 3β-acetoxybisnor-5-cholenic acid (1474-14-2)

Guidance literature:

With chloroform; ozone; Erwaermen des Reaktionsprodukts mit Zink und Essigsaeure;

DOI:10.1021/ja01200a035

Reference yield:

acetic acid stigmasteryl ester (4651-48-3,4651-49-4,54482-54-1,75082-06-3,80735-62-2) → 3β-acetoxybisnor-5-cholenic acid (1474-14-2)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrachloromethane; bromine

2: tetrachloromethane; chromium (VI)-oxide; aqueous acetic acid / Erwaermen des Reaktionsprodukts mit Zink-Pulver und Essigsaeure

With chromium(VI) oxide; tetrachloromethane; bromine; acetic acid;

upstream raw materials:

3β-acetoxy-23,24-bisnor-chol-5-en-22-ol

5α,6β-dibromostigmastan-3β-yl acetate

brassicasterol acetate

(10R)-3c-Acetoxy-10r.13c-dimethyl-17c-((1R:4R)-1.5-dimethyl-4-aethyl-hexen-(2t)-yl)-(8cH.9tH.14tH)-Δ⁵-tetradecahydro-1H-cyclopenta[a]phenanthren

Downstream raw materials:

3β-acetoxy-20(S)-5α-bisnorcholanic acid

3β-acetoxy-23,24-dinorchol-5-en-22-oyl chloride

Pregnenolone

(S)-2-((3S,8S,9S,10R,13S,14S,17R)-3-Acetoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-propionic acid 4-nitro-phenyl ester

Refernces

• 1、 -. "NEUROACTIVE STEROIDS, COMPOSITIONS, AND USES THEREOF". . . Retrieved 2016/02/16.
• 2、 Sato,Sonoda,Saito. "Synthesis of [21-2H]- and [22-2H]-derivatives of 23, 24, 25, 26, 27-pentanorcholesterol and 23, 24, 25, 26, 27-pentanordihydrolanosterol and the stereochemical significance of the deuterium spin-lattice relaxation times". . p. 1150 - 1156. Retrieved 2007/10/02.