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

Base Information

• Chemical Name: (-)-(1R,2R)-2-[(S)-(dimethylphenylsilyl)(phenyl)methyl]cyclopentyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate
• CAS No.: 196940-71-3
• Molecular Formula: C₂₈H₃₉NO₃Si
• Molecular Weight: 465.708
• Mol file: 196940-71-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about (-)-(1R,2R)-2-[(S)-(dimethylphenylsilyl)(phenyl)methyl]cyclopentyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate 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: 36.0%

phenyldimethylsilyl chloride (768-33-2) + (Z)-6-phenylhex-5-enyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate (196940-65-5) → exo-6-phenylbicyclo[3.1.0]hexane (58647-76-0) + (-)-(1R,2R)-2-[(S)-(dimethylphenylsilyl)(phenyl)methyl]cyclopentyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate (196940-71-3)

Guidance literature:

(Z)-6-phenylhex-5-enyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate; With sec.-butyllithium; (-)-sparteine; In diethyl ether; at -78 ℃; for 24h;

phenyldimethylsilyl chloride; In diethyl ether; at -78 - 20 ℃;

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]cyclopentyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate (196940-71-3)

Guidance literature:

Multi-step reaction with 3 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

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

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]cyclopentyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate (196940-71-3)

Guidance literature:

Multi-step reaction with 2 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

With potassium tert-butylate; sec.-butyllithium; (-)-sparteine; In diethyl ether; 1.1: Condensation / 2.1: carbolithiation / 2.2: Substitution;

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

upstream raw materials:

phenyldimethylsilyl chloride

(Z)-6-phenylhex-5-enyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate

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

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

Downstream raw materials:

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