rac-(9β,13αC¹⁵)-pimara-8(14),15-diene

Base Information

• Chemical Name: rac-(9β,13αC¹⁵)-pimara-8(14),15-diene
• CAS No.: 71030-08-5
• Molecular Formula: C₂₀H₃₂
• Molecular Weight: 272.474
• Mol file: 71030-08-5.mol

Synonyms:

Chemical Property of rac-(9β,13αC¹⁵)-pimara-8(14),15-diene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of rac-(9β,13αC¹⁵)-pimara-8(14),15-diene

There total 11 articles about rac-(9β,13αC¹⁵)-pimara-8(14),15-diene 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