(-)-(1R,2R)-2-[(S)-(dimethylphenylsilyl)(phenyl)methyl]cyclopentanol

Base Information

• Chemical Name: (-)-(1R,2R)-2-[(S)-(dimethylphenylsilyl)(phenyl)methyl]cyclopentanol
• CAS No.: 196940-77-9
• Molecular Formula: C₂₀H₂₆OSi
• Molecular Weight: 310.511
• Mol file: 196940-77-9.mol

Synonyms:(-)-(1R,2R)-2-[(S)-(dimethylphenylsilyl)(phenyl)methyl]cyclopentanol

Chemical Property of (-)-(1R,2R)-2-[(S)-(dimethylphenylsilyl)(phenyl)methyl]cyclopentanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(1R,2R)-2-[(S)-(dimethylphenylsilyl)(phenyl)methyl]cyclopentanol

There total 9 articles about (-)-(1R,2R)-2-[(S)-(dimethylphenylsilyl)(phenyl)methyl]cyclopentanol 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: 89.0%

(-)-(1R,2R)-2-[(S)-(dimethylphenylsilyl)(phenyl)methyl]cyclopentyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate (196940-71-3) → (-)-(1R,2R)-2-[(S)-(dimethylphenylsilyl)(phenyl)methyl]cyclopentanol (196940-77-9)

Guidance literature:

With methanesulfonic acid; potassium carbonate; In methanol; Heating;

DOI:10.1002/(SICI)1522-2675(19991110)82:11<1860::AID-HLCA1860>3.0.CO;2-8

Reference yield:

5-bromopentyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate (196940-78-0) → (-)-(1R,2R)-2-[(S)-(dimethylphenylsilyl)(phenyl)methyl]cyclopentanol (196940-77-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 95 percent / 5 h / 100 °C

2.1: 86 percent / t-BuOK / diethyl ether / 0.08 h / -40 °C

3.1: (-)-sparteine; s-BuLi / diethyl ether / 24 h / -78 °C

3.2: 36 percent / diethyl ether / -78 - 20 °C

4.1: 89 percent / MeSO₃H; K₂CO₃ / methanol / Heating

With methanesulfonic acid; potassium tert-butylate; sec.-butyllithium; potassium carbonate; (-)-sparteine; In methanol; diethyl ether; 1.1: Substitution / 2.1: Condensation / 3.1: carbolithiation / 3.2: Substitution / 4.1: deprotection;

DOI:10.1002/(SICI)1522-2675(19991110)82:11<1860::AID-HLCA1860>3.0.CO;2-8

Reference yield:

[5-(2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyloxy)pentyl]triphenylphosphonium bromide → (-)-(1R,2R)-2-[(S)-(dimethylphenylsilyl)(phenyl)methyl]cyclopentanol (196940-77-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 86 percent / t-BuOK / diethyl ether / 0.08 h / -40 °C

2.1: (-)-sparteine; s-BuLi / diethyl ether / 24 h / -78 °C

2.2: 36 percent / diethyl ether / -78 - 20 °C

3.1: 89 percent / MeSO₃H; K₂CO₃ / methanol / Heating

With methanesulfonic acid; potassium tert-butylate; sec.-butyllithium; potassium carbonate; (-)-sparteine; In methanol; diethyl ether; 1.1: Condensation / 2.1: carbolithiation / 2.2: Substitution / 3.1: deprotection;

DOI:10.1002/(SICI)1522-2675(19991110)82:11<1860::AID-HLCA1860>3.0.CO;2-8

upstream raw materials:

(-)-(1R,2R)-2-[(S)-(dimethylphenylsilyl)(phenyl)methyl]cyclopentyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate

phenyldimethylsilyl chloride

5-bromopentyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate

5-hydroxypentyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate