12-Deacetoxyscalaradial

Base Information

• Chemical Name: 12-Deacetoxyscalaradial
• CAS No.: 154554-90-2
• Molecular Formula: C₂₅H₃₈O₂
• Molecular Weight: 370.576
• DSSTox Substance ID: DTXSID70935012
• Nikkaji Number: J829.987K
• Wikidata: Q82911012
• Metabolomics Workbench ID: 137473
• ChEMBL ID: CHEMBL472023
• Mol file: 154554-90-2.mol

Synonyms:12-deacetoxyscalaradial

Chemical Property of 12-Deacetoxyscalaradial

Chemical Property:

• XLogP3: 6.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 370.287180451
• Heavy Atom Count: 27
• Complexity: 676

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(CCCC2(C1CCC3(C2CCC4(C3CC=C(C4C=O)C=O)C)C)C)C
• Isomeric SMILES: C[C@]12CCCC([C@@H]1CC[C@@]3([C@@H]2CC[C@]4([C@H]3CC=C([C@@H]4C=O)C=O)C)C)(C)C

Technology Process of 12-Deacetoxyscalaradial

There total 12 articles about 12-Deacetoxyscalaradial 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: 90.0%

((1R,4aS,4bR,6aS,10aS,10bR,12aS)-2-Hydroxymethyl-4b,7,7,10a,12a-pentamethyl-1,4,4a,4b,5,6,6a,7,8,9,10,10a,10b,11,12,12a-hexadecahydro-chrysen-1-yl)-methanol (183161-42-4) → 12-deacetoxyscalaradial (154554-90-2)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -50 ℃; for 1h;

DOI:10.1021/ja972690l

Reference yield:

(5aS,5bR,7aS,11aS,11bR,13aS,13bR)-5b,8,8,11a,13a-Pentamethyl-5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a,13b-hexadecahydro-1H-2-oxa-cyclopenta[a]chrysen-3-one (196938-03-1) → 12-deacetoxyscalaradial (154554-90-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / DIBAL-H / CH₂Cl₂ / 1 h / -78 - -20 °C

2: 90 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1 h / -50 °C

With oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In dichloromethane;

DOI:10.1021/ja972690l

Reference yield:

(1R,4aS,4bR,6aS,10aS,10bR,12aS)-1-[(Dimethyl-phenyl-silanyl)-methyl]-4b,7,7,10a,12a-pentamethyl-hexadecahydro-chrysen-2-one (196938-01-9) → 12-deacetoxyscalaradial (154554-90-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / KHMDS / tetrahydrofuran / 0.33 h / -78 °C

2: 1.) BF₃*2AcOH, 2.) KF, KHCO₃, H₂O₂, 3.) Pd(OAc)2, Pd⁽⁰⁾ 1,3-(bisdiphenylphosphino)propane, i-Pr₂NEt / 1) CHCl₃, 23 deg C, 5 h; 2) THF, MeOH, 0-23 deg C, 12 h; 3) DMF, 65 deg C, 5 h, 1 atm

3: 95 percent / DIBAL-H / CH₂Cl₂ / 1 h / -78 - -20 °C

4: 90 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1 h / -50 °C

With palladium diacetate; potassium fluoride; oxalyl dichloride; Pd⁽⁰⁾ 1,3-(bis(diphenylphosphino))propane; dihydrogen peroxide; boron trifluoride diacetate; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium hydrogencarbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja972690l

upstream raw materials:

((1R,4aS,4bR,6aS,10aS,10bR,12aS)-2-Hydroxymethyl-4b,7,7,10a,12a-pentamethyl-1,4,4a,4b,5,6,6a,7,8,9,10,10a,10b,11,12,12a-hexadecahydro-chrysen-1-yl)-methanol

(5aS,5bR,7aS,11aS,11bR,13aS,13bR)-5b,8,8,11a,13a-Pentamethyl-5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a,13b-hexadecahydro-1H-2-oxa-cyclopenta[a]chrysen-3-one

(1R,4aS,4bR,6aS,10aS,10bR,12aS)-1-[(Dimethyl-phenyl-silanyl)-methyl]-4b,7,7,10a,12a-pentamethyl-hexadecahydro-chrysen-2-one

(1R,4aS,4bR,6aR,8S,10aR,10bS,12aS)-1-[(Dimethyl-phenyl-silanyl)-methyl]-8-hydroxy-4b,7,7,10a,12a-pentamethyl-hexadecahydro-chrysen-2-one

Refernces

• 1、 Furuichi, Noriyuki,Hata, Toshiyuki,Soetjipto, Hartati,Kato, Mariko,Katsumura, Shigeo. "Common synthetic strategy for optically active cyclic terpenoids having a 1,1,5-trimethyl-trans-decalin nucleus: Syntheses of (+)-acuminolide, (-)-spongianolide A, and (+)-scalarenedial". . p. 8425 - 8442. Retrieved 2007/10/03.