{(1R,2R,3R)-2-[(3E)-4,8-dimethylnona-3,7-dien-1-yl]-2-methyl-3-[(1E,5E)-2,6,10-trimethylundeca-1,5,9-trien-1-yl]cyclopropyl}methyl trihydrogen diphosphate

Base Information

• Chemical Name: {(1R,2R,3R)-2-[(3E)-4,8-dimethylnona-3,7-dien-1-yl]-2-methyl-3-[(1E,5E)-2,6,10-trimethylundeca-1,5,9-trien-1-yl]cyclopropyl}methyl trihydrogen diphosphate
• CAS No.: 22477-86-7
• Molecular Formula: C₃₀H₅₂O₇P₂
• Molecular Weight: 586.686
• Mol file: 22477-86-7.mol

Synonyms:

Chemical Property of {(1R,2R,3R)-2-[(3E)-4,8-dimethylnona-3,7-dien-1-yl]-2-methyl-3-[(1E,5E)-2,6,10-trimethylundeca-1,5,9-trien-1-yl]cyclopropyl}methyl trihydrogen diphosphate

Chemical Property:

• Vapor Pressure: 2.04E-19mmHg at 25°C

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(1R,2R,3R)-2-[(3E)-4,8-dimethylnona-3,7-dien-1-yl]-2-methyl-3-[(1E,5E)-2,6,10-trimethylundeca-1,5,9-trien-1-yl]cyclopropyl}methyl trihydrogen diphosphate

There total 5 articles about {(1R,2R,3R)-2-[(3E)-4,8-dimethylnona-3,7-dien-1-yl]-2-methyl-3-[(1E,5E)-2,6,10-trimethylundeca-1,5,9-trien-1-yl]cyclopropyl}methyl trihydrogen diphosphate 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: 22.0%

Presqualene alcohol (117182-28-2) → (E)-presqualene (22477-86-7,30516-84-8)

Guidance literature:

With tetrabutylammonium dihydrogen phosphate; In acetonitrile; for 2h; Ambient temperature;

DOI:10.1021/jo00109a026

Reference yield: 10.0%

Presqualene alcohol (31908-49-3) → (+)-(1R,2R,3R)-Presqualene monophosphate + (+)-(1R,2R,3R)-Presqualene diphosphate (22477-86-7,30516-84-8)

Guidance literature:

With tetrabutylammonium dihydrogen phosphate; In acetonitrile; for 1h; Ambient temperature;

DOI:10.1021/jo00109a026

Reference yield:

farnesyl pyrophosphate (372-97-4,13058-04-3,25744-33-6,27248-37-9,27248-38-0,40716-68-5) → (+)-(1R,2R,3R)-Presqualene diphosphate (22477-86-7,30516-84-8)

Guidance literature:

With baker's yeast pyrophosphatase; recombinant human squalene synthase; sodium chloride; magnesium chloride; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid; In water; at 20 ℃; for 8h; pH=7.4; Enzymatic reaction;

DOI:10.1073/pnas.1010907107

upstream raw materials:

Presqualene alcohol

farnesyl pyrophosphate

Presqualene alcohol

farnesyl pyrophosphate

Downstream raw materials:

Despyrophosphoryl-praesqualen

(6E,10E,16E)-2,6,10,13,17,21-hexamethyl-13-vinyl-docosa-2,6,10,16,20-pentaene

Refernces

• 1、 Rogers,Yi,Poulter. "Enantioselective synthesis of (+)-presqualene diphosphate". . p. 941 - 945. Retrieved 1995.