(3R)-3-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-Dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]butanenitrile

Base Information

• Chemical Name: (3R)-3-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-Dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]butanenitrile
• CAS No.: 118316-12-4
• Molecular Formula: C₂₃H₃₇NO₂
• Molecular Weight: 359.552
• European Community (EC) Number: 828-107-5
• DSSTox Substance ID: DTXSID20450260
• Wikidata: Q76416345
• Mol file: 118316-12-4.mol

Synonyms:118316-12-4;(3R)-3-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-Dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]butanenitrile;SCHEMBL15477473;(3|A,5|A,7|A)-3,7-Dihydroxy-24norcholane-23-nitrile;DTXSID20450260;IYRKNDIHBKVMOV-KHLWDBHXSA-N

Chemical Property of (3R)-3-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-Dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]butanenitrile

Chemical Property:

• Boiling Point: 514.2±25.0 °C(Predicted)
• PKA: 14.77±0.70(Predicted)
• PSA: 64.25000
• Density: 1.089±0.06 g/cm3(Predicted)
• LogP: 4.52678
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 359.282429423
• Heavy Atom Count: 26
• Complexity: 596

Purity/Quality:

99.9% ^*data from raw suppliers

(3α,5β,7β)-3,7-Dihydroxy-24-norcholane-23-nitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CC#N)C1CCC2C1(CCC3C2C(CC4C3(CCC(C4)O)C)O)C
• Isomeric SMILES: C[C@H](CC#N)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C
• Uses: (3α,5β,7β)-3,7-Dihydroxy-24norcholane-23-nitrile is used in the preparation of ursodeoxycholic acid amides as glucocorticoid receptor modulators.

Technology Process of (3R)-3-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-Dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]butanenitrile

There total 2 articles about (3R)-3-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-Dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]butanenitrile 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: 80.0%

(R)-4-((3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-bis(formyloxy)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid (6058-15-7,6159-50-8) → 3α,7β-dihydroxy-24-nor-5β-cholan-23-nitrile (118316-12-4)

Guidance literature:

(R)-4-((3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-bis(formyloxy)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid; With trifluoroacetic acid; trifluoroacetic anhydride; sodium nitrite; at 15 - 48 ℃;

With water; sodium hydroxide; In ethanol; n-heptane;

Reference yield:

3α,7β-diformyloxy-24-nor-5β-cholan-23-nitrile (118316-07-7) → 3α,7β-dihydroxy-24-nor-5β-cholan-23-nitrile (118316-12-4)

Guidance literature:

With water; sodium hydroxide; In ethanol; n-heptane; at 55 - 65 ℃; for 1.5h;

Reference yield:

3α,7β-dihydroxy-24-nor-5β-cholan-23-nitrile (118316-12-4) → Norursodeoxycholic acid (99697-24-2)

Guidance literature:

3α,7β-dihydroxy-24-nor-5β-cholan-23-nitrile; With sodium hydroxide; In propan-1-ol; for 20h; Autoclave; Reflux;

With hydrogenchloride; at 55 - 65 ℃; pH=1 - 2;

upstream raw materials:

(R)-4-((3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-bis(formyloxy)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid

3α,7β-diformyloxy-24-nor-5β-cholan-23-nitrile

Downstream raw materials:

Norursodeoxycholic acid