(4R)-1-(Trimethylsilyl)-4-(trimethylsilyloxy)-L-proline trimethylsilyl ester

Base Information

• Chemical Name: (4R)-1-(Trimethylsilyl)-4-(trimethylsilyloxy)-L-proline trimethylsilyl ester
• CAS No.: 55429-66-8
• Molecular Formula: C₁₄H₃₃NO₃Si₃
• Molecular Weight: 347.677
• Mol file: 55429-66-8.mol

Synonyms:(4R)-1-(Trimethylsilyl)-4-(trimethylsilyloxy)-L-proline trimethylsilyl ester

Chemical Property of (4R)-1-(Trimethylsilyl)-4-(trimethylsilyloxy)-L-proline trimethylsilyl ester

Chemical Property:

• Boiling Point: 323.8±42.0 °C(Predicted)
• PKA: 7.53±0.60(Predicted)
• PSA: 38.77000
• Density: 0.95±0.1 g/cm3(Predicted)
• LogP: 3.43170

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (4R)-1-(Trimethylsilyl)-4-(trimethylsilyloxy)-L-proline trimethylsilyl ester

There total 1 articles about (4R)-1-(Trimethylsilyl)-4-(trimethylsilyloxy)-L-proline trimethylsilyl ester 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: 86.0%

N,O-bis-(trimethylsilyl)-acetamide (10416-59-8) + 4R-4-hydroxyproline (51-35-4,30724-02-8) → N-(trimethylsilyl) acetimidate + trimethylsilyl (2S,4R)-N-trimethylsilyl-4-(trimethylsilyloxy)pyrrolidine-2-carboxylate (55429-66-8)

Guidance literature:

at 90 - 100 ℃; for 6h; Inert atmosphere;

DOI:10.1021/jo1025783

Reference yield:

trimethylsilyl (2S,4R)-N-trimethylsilyl-4-(trimethylsilyloxy)pyrrolidine-2-carboxylate (55429-66-8) → (2S,4S)-N-chloroacetyl-4-fluoropyrrolidine-2-carboxamide (596817-05-9)

Guidance literature:

Multi-step reaction with 4 steps

1: dichloromethane / 2 h / 20 °C / Inert atmosphere

2: hydrogen fluoride / acetonitrile / 15 h / 20 °C / Inert atmosphere

3: 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride / dichloromethane / 73 h / 0 - 20 °C / Inert atmosphere

4: ammonia / dichloromethane; water / 0.5 h / 20 °C / Inert atmosphere; Cooling with ice

With 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride; hydrogen fluoride; ammonia; In dichloromethane; water; acetonitrile;

DOI:10.1021/jo1025783

Reference yield:

trimethylsilyl (2S,4R)-N-trimethylsilyl-4-(trimethylsilyloxy)pyrrolidine-2-carboxylate (55429-66-8) → (2S,4S)-1-(2-chloroacetyl)-4-fluoropyrrolidine-2-carbonitrile (596817-06-0)

Guidance literature:

Multi-step reaction with 5 steps

1: dichloromethane / 2 h / 20 °C / Inert atmosphere

2: hydrogen fluoride / acetonitrile / 15 h / 20 °C / Inert atmosphere

3: 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride / dichloromethane / 73 h / 0 - 20 °C / Inert atmosphere

4: ammonia / dichloromethane; water / 0.5 h / 20 °C / Inert atmosphere; Cooling with ice

5: trifluoroacetic anhydride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

With 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride; hydrogen fluoride; ammonia; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane; water; acetonitrile;

DOI:10.1021/jo1025783

upstream raw materials:

N,O-bis-(trimethylsilyl)-acetamide

4R-4-hydroxyproline

Downstream raw materials:

(2S,4S)-1-(2-chloroacetyl)-4-fluoropyrrolidine-2-carbonitrile

(2S,4S)-N-chloroacetyl-4-fluoropyrrolidine-2-carboxamide