(2R,3S)-N-benzoyl-O-<<2-(trimethylsilyl)ethoxy>methyl>-3-phenylisoserine methyl ester

Base Information

• Chemical Name: (2R,3S)-N-benzoyl-O-<<2-(trimethylsilyl)ethoxy>methyl>-3-phenylisoserine methyl ester
• CAS No.: 99458-19-2
• Molecular Formula: C₂₃H₃₁NO₅Si
• Molecular Weight: 429.588
• Mol file: 99458-19-2.mol

Synonyms:(2R,3S)-N-benzoyl-O-<<2-(trimethylsilyl)ethoxy>methyl>-3-phenylisoserine methyl ester

Chemical Property of (2R,3S)-N-benzoyl-O-<<2-(trimethylsilyl)ethoxy>methyl>-3-phenylisoserine methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-N-benzoyl-O-<<2-(trimethylsilyl)ethoxy>methyl>-3-phenylisoserine methyl ester

There total 5 articles about (2R,3S)-N-benzoyl-O-<<2-(trimethylsilyl)ethoxy>methyl>-3-phenylisoserine methyl 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: 96.0%

methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate (32981-85-4) + (2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) → (2R,3S)-N-benzoyl-O-<<2-(trimethylsilyl)ethoxy>methyl>-3-phenylisoserine methyl ester (99458-19-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 40h;

DOI:10.1021/jo00351a008

Reference yield:

Methyl (2R,3S)-(+)-2-hydroxy-3-azido-3-phenyl-propionate (99458-15-8) → (2R,3S)-N-benzoyl-O-<<2-(trimethylsilyl)ethoxy>methyl>-3-phenylisoserine methyl ester (99458-19-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / triethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h

2: 1.) H₂ / 1.) 10percent Pd/C / 1.) CH₃OH, 15 h, 2.) CH₃OH, RT, 72 h

3: 96 percent / ethyldiisopropylamine / CH₂Cl₂ / 40 h

With dmap; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In dichloromethane;

DOI:10.1021/jo00351a008

Reference yield:

(2R,3R)-(+)-methyl 3-phenyloxiranecarboxylate (99528-65-1) → (2R,3S)-N-benzoyl-O-<<2-(trimethylsilyl)ethoxy>methyl>-3-phenylisoserine methyl ester (99458-19-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / azidotrimethylsilane, zinc chloride / 48 h / 68 °C

2: 94 percent / triethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h

3: 1.) H₂ / 1.) 10percent Pd/C / 1.) CH₃OH, 15 h, 2.) CH₃OH, RT, 72 h

4: 96 percent / ethyldiisopropylamine / CH₂Cl₂ / 40 h

With dmap; trimethylsilylazide; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; zinc(II) chloride; palladium on activated charcoal; In dichloromethane;

DOI:10.1021/jo00351a008

upstream raw materials:

methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

(2-trimethylethylsilylethoxy)methyl chloride

Methyl (2R,3S)-(+)-2-hydroxy-3-azido-3-phenyl-propionate

(2R,3R)-(+)-methyl 3-phenyloxiranecarboxylate

Downstream raw materials:

C₄₂H₅₁NO₁₀Si

C₃₆H₃₇NO₉

(2R,3S)-N-benzoyl-O-<<2-(trimethylsilyl)ethoxy>methyl>-3-phenylisoserine

Refernces