(-)-(1'R,2'S)-2-(2'-tert-butyldiphenylsilyloxymethylcyclopent-4'-enyl)propan-2-ol

Base Information

• Chemical Name: (-)-(1'R,2'S)-2-(2'-tert-butyldiphenylsilyloxymethylcyclopent-4'-enyl)propan-2-ol
• CAS No.: 137567-94-3
• Molecular Formula: C₂₅H₃₄O₂Si
• Molecular Weight: 394.629
• Mol file: 137567-94-3.mol

Synonyms:(-)-(1'R,2'S)-2-(2'-tert-butyldiphenylsilyloxymethylcyclopent-4'-enyl)propan-2-ol

Chemical Property of (-)-(1'R,2'S)-2-(2'-tert-butyldiphenylsilyloxymethylcyclopent-4'-enyl)propan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(1'R,2'S)-2-(2'-tert-butyldiphenylsilyloxymethylcyclopent-4'-enyl)propan-2-ol

There total 4 articles about (-)-(1'R,2'S)-2-(2'-tert-butyldiphenylsilyloxymethylcyclopent-4'-enyl)propan-2-ol 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: 72.0%

(-)-(1'R,2'S)-2-(2'-hydroxymethylcyclopent-4'-enyl)propan-2-ol (137503-35-6) + tert-butylchlorodiphenylsilane (58479-61-1) → (-)-(1'R,2'S)-2-(2'-tert-butyldiphenylsilyloxymethylcyclopent-4'-enyl)propan-2-ol (137567-94-3)

Guidance literature:

With triethylamine; dmap; In dichloromethane; for 16h; Ambient temperature;

DOI:10.1039/P19910002385

Reference yield:

(+/-)-7,7-dimethylbicyclo<3.2.0>hept-2-en-6-one (767-85-1,100853-05-2,100898-02-0,100898-03-1) → (-)-(1'R,2'S)-2-(2'-tert-butyldiphenylsilyloxymethylcyclopent-4'-enyl)propan-2-ol (137567-94-3)

Guidance literature:

Multi-step reaction with 3 steps

1: O₂ (air) / H₂O; dimethylformamide / 4 h / 30 °C / biosynthesis by Acinetobacter NCIMB 9871

2: 89 percent / lithium aluminum hydride / diethyl ether / 3 h / Ambient temperature

3: 72 percent / triethylamine / N,N-dimethylaminopyridine / CH₂Cl₂ / 16 h / Ambient temperature

With lithium aluminium tetrahydride; oxygen; triethylamine; dmap; In diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1039/P19910002385

Reference yield:

(+)-(1R,5S)-7,7-dimethylbicyclo<3.2.0>hept-2-en-6-one (100898-02-0) → (-)-(1'R,2'S)-2-(2'-tert-butyldiphenylsilyloxymethylcyclopent-4'-enyl)propan-2-ol (137567-94-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 56 percent / 30percent aq. hydrogen peroxide / acetic acid / 48 h / 0 - 5 °C

2: 89 percent / lithium aluminum hydride / diethyl ether / 3 h / Ambient temperature

3: 72 percent / triethylamine / N,N-dimethylaminopyridine / CH₂Cl₂ / 16 h / Ambient temperature

With lithium aluminium tetrahydride; dihydrogen peroxide; triethylamine; dmap; In diethyl ether; dichloromethane; acetic acid;

DOI:10.1039/P19910002385

upstream raw materials:

(-)-(1'R,2'S)-2-(2'-hydroxymethylcyclopent-4'-enyl)propan-2-ol

tert-butylchlorodiphenylsilane

(+/-)-7,7-dimethylbicyclo<3.2.0>hept-2-en-6-one

(+)-(1R,5S)-7,7-dimethylbicyclo<3.2.0>hept-2-en-6-one

Refernces