Ent-sandaracopimaradiene

Base Information

• Chemical Name: Ent-sandaracopimaradiene
• CAS No.: 21738-16-9
• Molecular Formula: C₂₀H₃₂
• Molecular Weight: 272.474
• DSSTox Substance ID: DTXSID40487437
• Metabolomics Workbench ID: 28523,57313
• Nikkaji Number: J16.237J
• Wikidata: Q27104747
• Mol file: 21738-16-9.mol

Synonyms:ent-sandaracopimaradiene

Chemical Property of Ent-sandaracopimaradiene

Chemical Property:

• Vapor Pressure: 0.000211mmHg at 25°C
• Boiling Point: 337°C at 760 mmHg
• Flash Point: 150.5°C
• PSA: 0.00000
• Density: 0.93g/cm³
• LogP: 6.14150
• XLogP3: 7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 272.250401021
• Heavy Atom Count: 20
• Complexity: 441

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCCC2(C1CCC3=CC(CCC32)(C)C=C)C)C
• Isomeric SMILES: C[C@]1(CC[C@@H]2C(=C1)CC[C@H]3[C@]2(CCCC3(C)C)C)C=C

Technology Process of Ent-sandaracopimaradiene

There total 11 articles about Ent-sandaracopimaradiene 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:

(1R,4aR,4bS,7R,10aR)-1,4a,7-Trimethyl-1-phenylsulfanylmethyl-7-vinyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydro-phenanthrene (142699-02-3) → sandaracopimaradiene (1686-61-9,5956-33-2,17123-77-2,19882-10-1,21738-16-9,71030-08-5,1686-56-2)

Guidance literature:

With lithium-sodium alloy; ammonia; In tetrahydrofuran; at -33 ℃;

DOI:10.1021/jo00043a013

Reference yield:

(E,E,E)-geranylgeranyl diphosphate (6699-20-3,13100-78-2,64732-91-8) → sandaracopimaradiene (1686-61-9,5956-33-2,17123-77-2,19882-10-1,21738-16-9,71030-08-5,1686-56-2)

Guidance literature:

With recombinant cyclase from A_. niger; In aq. phosphate buffer; at 16 ℃; for 72h; pH=7; Reagent/catalyst; Enzymatic reaction;

DOI:10.1021/acs.jnatprod.6b00764

Reference yield:

methyl sandaracopimarate (1686-54-0) → sandaracopimaradiene (1686-61-9,5956-33-2,17123-77-2,19882-10-1,21738-16-9,71030-08-5,1686-56-2)

Guidance literature:

Multi-step reaction with 4 steps

1: LiAlH₄ / diethyl ether / Ambient temperature

2: Et₃N / CH₂Cl₂ / 0 °C

3: 1) NaH / 1) DMF, 5 min, 2) DMF, 120-130 deg C

4: Li/Na, liq. NH₃ / tetrahydrofuran / -33 °C

With lithium aluminium tetrahydride; lithium-sodium alloy; ammonia; sodium hydride; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jo00043a013

upstream raw materials:

(1R,4aR,4bS,7R,10aR)-1,4a,7-Trimethyl-1-phenylsulfanylmethyl-7-vinyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydro-phenanthrene

methyl sandaracopimarate

sandaracopimara-8⁽¹⁴⁾,15-dien-18-ol

Methanesulfonic acid (1R,4aR,4bS,7R,10aR)-1,4a,7-trimethyl-7-vinyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydro-phenanthren-1-ylmethyl ester

Downstream raw materials:

isopimara-8,15-diene

sandaracopimara-8⁽¹⁴⁾,15-dien-18-ol

Refernces

• 1、 Morrone, Dana,Hillwig, Matthew L.,Mead, Matthew E.,Lowry, Luke,Fulton, D. Bruce,Peters, Reuben J.. "Evident and latent plasticity across the rice diterpene synthase family with potential implications for the evolution of diterpenoid metabolism in the cereals". scheme or table. p. 589 - 595. Retrieved 2012/03/08.