Sarcophytol A

Base Information

• Chemical Name: Sarcophytol A
• CAS No.: 72629-69-7
• Deprecated CAS: 88979-97-9
• Molecular Formula: C₂₀H₃₂O
• Molecular Weight: 288.473
• Hs Code.: 2906199090
• UNII: 240025685W
• DSSTox Substance ID: DTXSID5021257
• Wikidata: Q27253783
• Metabolomics Workbench ID: 143725
• ChEMBL ID: CHEMBL462849
• Mol file: 72629-69-7.mol

Synonyms:(1S,2Z,4E,8E,12E)-2-Isopropyl-5,9,13-trimethyl-2,4,8,12-cyclotetradecatetraen-1-ol;sarcophytol A

Chemical Property of Sarcophytol A

Chemical Property:

• Vapor Pressure: 1.23E-08mmHg at 25°C
• Boiling Point: 415.4°C at 760 mmHg
• Flash Point: 175.5°C
• PSA: 20.23000
• Density: 0.894g/cm³
• LogP: 5.73270
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 288.245315640
• Heavy Atom Count: 21
• Complexity: 447

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCCC(=CC=C(C(CC(=CCC1)C)O)C(C)C)C
• Isomeric SMILES: C/C/1=C\CC/C(=C/C=C(\[C@H](C/C(=C/CC1)/C)O)/C(C)C)/C

Technology Process of Sarcophytol A

There total 27 articles about Sarcophytol A 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: 92.0%

(5E,9E,11Z)-(R)-2-Isopropenyl-12-isopropyl-5,9-dimethyl-oxacyclotrideca-5,9,11-triene (153744-68-4) → Sarcophytol A (72629-69-7,88979-97-9)

Guidance literature:

With tert.-butyl lithium; In tetrahydrofuran; at -78 - 0 ℃;

DOI:10.1016/S0040-4039(00)61357-6

Reference yield: 72.0%

(2Z,4E,8E,12E)-2-(1-Methylethyl)-5,9,13-trimethyl-2,4,8,12-cyclotetradecatetraen-1-one (77394-15-1) → Sarcophytol A (72629-69-7,88979-97-9)

Guidance literature:

With lithium aluminium tetrahydride; (S)-2-(2,6-xylidinomethyl)pyrrolidine; In diethyl ether; at -72 ℃; for 6h;

DOI:10.1021/jo00089a011

Reference yield:

Farnesal (502-67-0) → Sarcophytol A (72629-69-7,88979-97-9)

Guidance literature:

Multi-step reaction with 7 steps

1: n-BuLi / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) 0 deg C, 5 h

2: SeO₂, 2-hydroxybenzoic acid, 80percent t-BuOOH / CH₂Cl₂ / 30 h / Ambient temperature

3: 79 percent / 1 M DIBAL / toluene / 0.5 h / -78 °C

4: 95 percent / BaMnO₄ / CH₂Cl₂ / 8 h / Ambient temperature

5: 100 percent / KCN/18-crown-6 complex / 2 h / 0 °C

6: 15 percent / 1 M LiN(SiMe₃)2 / tetrahydrofuran / 0.33 h / 55 °C

7: 72 percent / LiAlH₄, (S)-2-(2,6-xylidinomethyl)pyrrolidine / diethyl ether / 6 h / -72 °C

With tert.-butylhydroperoxide; lithium aluminium tetrahydride; n-butyllithium; selenium(IV) oxide; barium permanganate; (S)-2-(2,6-xylidinomethyl)pyrrolidine; diisobutylaluminium hydride; salicylic acid; lithium hexamethyldisilazane; potassium cyanide; 18-crown-6 ether; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;

DOI:10.1021/jo00089a011

upstream raw materials:

(2Z,4E,8E,12E)-2-(1-Methylethyl)-5,9,13-trimethyl-2,4,8,12-cyclotetradecatetraen-1-one

(5E,9E,11Z)-(R)-2-Isopropenyl-12-isopropyl-5,9-dimethyl-oxacyclotrideca-5,9,11-triene

(1Z,3E,7E,11S,12S,14S)-11,12-epoxy cembra-1,3,7-trien-14-ol

Farnesal

Refernces

• 1、 Takayanagi, Hisao,Sugiyama, Shigeo,Morinaka, Yasuhiro. "A ketal Claisen rearrangement for α-ketol isoprene unit elongation: application to a practical synthesis of sarcophytol A intermediate". . p. 751 - 756. Retrieved 2007/10/02.
• 2、 Kodama, Mitsuaki,Yoshio, Suzuyo,Yamaguchi, Shinji,Fukuyama, Yoshiyasu,Takayanagi, Hisao,et al.. "Total Syntheses of Both Enantiomers of Sarcophytols A and T Based on Stereospecific Wittig Rearrangement". . p. 8453 - 8456. Retrieved 2007/10/02.