(R)-2-[(4E,8E)-(S)-10-Benzyloxy-1-(1-ethoxy-ethoxy)-4,8-dimethyl-deca-4,8-dienyl]-2-methyl-oxirane

Base Information

• Chemical Name: (R)-2-[(4E,8E)-(S)-10-Benzyloxy-1-(1-ethoxy-ethoxy)-4,8-dimethyl-deca-4,8-dienyl]-2-methyl-oxirane
• CAS No.: 733010-76-9
• Molecular Formula: C₂₆H₄₀O₄
• Molecular Weight: 416.601
• Mol file: 733010-76-9.mol

Synonyms:(R)-2-[(4E,8E)-(S)-10-Benzyloxy-1-(1-ethoxy-ethoxy)-4,8-dimethyl-deca-4,8-dienyl]-2-methyl-oxirane

Chemical Property of (R)-2-[(4E,8E)-(S)-10-Benzyloxy-1-(1-ethoxy-ethoxy)-4,8-dimethyl-deca-4,8-dienyl]-2-methyl-oxirane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-[(4E,8E)-(S)-10-Benzyloxy-1-(1-ethoxy-ethoxy)-4,8-dimethyl-deca-4,8-dienyl]-2-methyl-oxirane

There total 3 articles about (R)-2-[(4E,8E)-(S)-10-Benzyloxy-1-(1-ethoxy-ethoxy)-4,8-dimethyl-deca-4,8-dienyl]-2-methyl-oxirane 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: 97.5%

ethyl vinyl ether (109-92-2,25104-37-4) + (4E,8E)-(S)-10-Benzyloxy-4,8-dimethyl-1-((R)-2-methyl-oxiranyl)-deca-4,8-dien-1-ol (733010-75-8) → (R)-2-[(4E,8E)-(S)-10-Benzyloxy-1-(1-ethoxy-ethoxy)-4,8-dimethyl-deca-4,8-dienyl]-2-methyl-oxirane (733010-76-9)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane;

DOI:10.1016/j.tetlet.2004.04.139

Reference yield:

(2E,6E,10E)-1-Benzyloxy-3,7,11-trimethyldodeca-2,6,10-trien-12-ol (71135-48-3) → (R)-2-[(4E,8E)-(S)-10-Benzyloxy-1-(1-ethoxy-ethoxy)-4,8-dimethyl-deca-4,8-dienyl]-2-methyl-oxirane (733010-76-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 4 Angstroem molecular sieves; L-(+)DIPT; Ti(O-i-Pr)4 / TBHP / CH₂Cl₂

1.2: PPh₃; I₂; H₂O / pyridine / acetonitrile; diethyl ether

2.1: 4 Angstroem molecular sieves; L-(+)DIPT; Ti(O-i-Pr)4 / TBHP / CH₂Cl₂

3.1: 97.5 percent / PPTS / CH₂Cl₂

With titanium(IV) isopropylate; L-(+)-diisopropyl tartrate; 4 A molecular sieve; pyridinium p-toluenesulfonate; tert.-butylhydroperoxide; In dichloromethane; 1.1: Sharpless asymmetric epoxidation / 2.1: Sharpless asymmetric epoxidation;

DOI:10.1016/j.tetlet.2004.04.139

Reference yield:

(6E,10E)-(S)-12-Benzyloxy-2,6,10-trimethyl-dodeca-1,6,10-trien-3-ol (733010-74-7) → (R)-2-[(4E,8E)-(S)-10-Benzyloxy-1-(1-ethoxy-ethoxy)-4,8-dimethyl-deca-4,8-dienyl]-2-methyl-oxirane (733010-76-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 4 Angstroem molecular sieves; L-(+)DIPT; Ti(O-i-Pr)4 / TBHP / CH₂Cl₂

2: 97.5 percent / PPTS / CH₂Cl₂

With titanium(IV) isopropylate; L-(+)-diisopropyl tartrate; 4 A molecular sieve; pyridinium p-toluenesulfonate; tert.-butylhydroperoxide; In dichloromethane; 1: Sharpless asymmetric epoxidation;

DOI:10.1016/j.tetlet.2004.04.139

upstream raw materials:

ethyl vinyl ether

(4E,8E)-(S)-10-Benzyloxy-4,8-dimethyl-1-((R)-2-methyl-oxiranyl)-deca-4,8-dien-1-ol

(2E,6E,10E)-1-Benzyloxy-3,7,11-trimethyldodeca-2,6,10-trien-12-ol

(6E,10E)-(S)-12-Benzyloxy-2,6,10-trimethyl-dodeca-1,6,10-trien-3-ol

Downstream raw materials:

(7E,11E)-(3R,4S)-13-Benzyloxy-4-(1-ethoxy-ethoxy)-3-hydroxy-3,7,11-trimethyl-trideca-7,11-dienenitrile

2-[(4R,5S)-5-((3E,7E)-9-Benzyloxy-3,7-dimethyl-nona-3,7-dienyl)-2,2,4-trimethyl-[1,3]dioxolan-4-yl]-ethanol

{2-[(4R,5S)-5-((3E,7E)-9-Benzyloxy-3,7-dimethyl-nona-3,7-dienyl)-2,2,4-trimethyl-[1,3]dioxolan-4-yl]-ethoxy}-tert-butyl-dimethyl-silane