(S)-4-((R)-2-Cyano-1-trimethylsilanyloxy-ethyl)-5-oxo-oxazolidine-3-carboxylic acid benzyl ester

Base Information

• Chemical Name: (S)-4-((R)-2-Cyano-1-trimethylsilanyloxy-ethyl)-5-oxo-oxazolidine-3-carboxylic acid benzyl ester
• CAS No.: 110545-07-8
• Molecular Formula: C₁₇H₂₂N₂O₅Si
• Molecular Weight: 362.458
• Mol file: 110545-07-8.mol

Synonyms:(S)-4-((R)-2-Cyano-1-trimethylsilanyloxy-ethyl)-5-oxo-oxazolidine-3-carboxylic acid benzyl ester

Chemical Property of (S)-4-((R)-2-Cyano-1-trimethylsilanyloxy-ethyl)-5-oxo-oxazolidine-3-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-((R)-2-Cyano-1-trimethylsilanyloxy-ethyl)-5-oxo-oxazolidine-3-carboxylic acid benzyl ester

There total 1 articles about (S)-4-((R)-2-Cyano-1-trimethylsilanyloxy-ethyl)-5-oxo-oxazolidine-3-carboxylic acid benzyl 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: 44.0%

trimethylsilyl cyanide (7677-24-9) + (S)-3-Benzyloxycarbonyl-5-oxo-4-(1,2-epoxyethyl)-oxazolidine (110545-05-6,110545-06-7) → (S)-4-((S)-2-Cyano-1-trimethylsilanyloxy-ethyl)-5-oxo-oxazolidine-3-carboxylic acid benzyl ester (110545-08-9) + (S)-4-((R)-2-Cyano-1-trimethylsilanyloxy-ethyl)-5-oxo-oxazolidine-3-carboxylic acid benzyl ester (110545-07-8)

Guidance literature:

With diethylaluminium chloride; In hexane; for 120h; Ambient temperature;

DOI:10.1055/s-1986-31863

Reference yield: 97.0%

(S)-4-((R)-2-Cyano-1-trimethylsilanyloxy-ethyl)-5-oxo-oxazolidine-3-carboxylic acid benzyl ester (110545-07-8) → (S)-3-Benzyloxycarbonyl-5-oxooxazolidine-4-<(R)-β-hydroxypropanenitrile> (110545-09-0)

Guidance literature:

With hydrogenchloride; In methanol; at 0 ℃; for 0.333333h;

DOI:10.1055/s-1986-31863

Reference yield:

(S)-4-((R)-2-Cyano-1-trimethylsilanyloxy-ethyl)-5-oxo-oxazolidine-3-carboxylic acid benzyl ester (110545-07-8) → (2S,3R)-N-Benzyloxycarbonyl-3-hydroxyglutamine (110657-89-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / 5percent aq. HCl / methanol / 0.33 h / 0 °C

2: 85 percent / 30percent aq. H₂O₂, 10percent aq. KOH / methanol / 72 h / Ambient temperature

With hydrogenchloride; potassium hydroxide; dihydrogen peroxide; In methanol;

DOI:10.1055/s-1986-31863

upstream raw materials:

trimethylsilyl cyanide

(S)-3-Benzyloxycarbonyl-5-oxo-4-(1,2-epoxyethyl)-oxazolidine

Downstream raw materials:

(S)-3-Benzyloxycarbonyl-5-oxooxazolidine-4-<(R)-β-hydroxypropanenitrile>

(2S,3R)-N-Benzyloxycarbonyl-3-hydroxyglutamine