(2R,3R)-1-benzyloxycarbonyl-3-methyl-2-aziridinecarboxylic acid methyl ester

Base Information

• Chemical Name: (2R,3R)-1-benzyloxycarbonyl-3-methyl-2-aziridinecarboxylic acid methyl ester
• CAS No.: 85550-10-3
• Molecular Formula: C₁₃H₁₅NO₄
• Molecular Weight: 249.266
• Mol file: 85550-10-3.mol

Synonyms:(2R,3R)-1-benzyloxycarbonyl-3-methyl-2-aziridinecarboxylic acid methyl ester

Chemical Property of (2R,3R)-1-benzyloxycarbonyl-3-methyl-2-aziridinecarboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-1-benzyloxycarbonyl-3-methyl-2-aziridinecarboxylic acid methyl ester

There total 5 articles about (2R,3R)-1-benzyloxycarbonyl-3-methyl-2-aziridinecarboxylic acid 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:

(2R,3R)-1-trityl-3-methyl-2-aziridinecarboxylic acid methyl ester (85550-09-0) → (2R,3R)-1-benzyloxycarbonyl-3-methyl-2-aziridinecarboxylic acid methyl ester (85550-10-3)

Guidance literature:

Multi-step reaction with 2 steps

1: TFA / CH₂Cl₂; methanol

2: NaHCO₃ / ethyl acetate

With sodium hydrogencarbonate; trifluoroacetic acid; In methanol; dichloromethane; ethyl acetate;

DOI:10.1021/ol0507930

Reference yield:

N-trityl-D-threonine methyl ester (85482-79-7) → (2R,3R)-1-benzyloxycarbonyl-3-methyl-2-aziridinecarboxylic acid methyl ester (85550-10-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / MsCl; Et₃N / tetrahydrofuran / Heating

2: TFA / CH₂Cl₂; methanol

3: NaHCO₃ / ethyl acetate

With sodium hydrogencarbonate; methanesulfonyl chloride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;

DOI:10.1021/ol0507930

Reference yield:

(2R,3S)-3-Methanesulfonyloxy-2-(trityl-amino)-butyric acid methyl ester (85482-83-3) → (2R,3R)-1-benzyloxycarbonyl-3-methyl-2-aziridinecarboxylic acid methyl ester (85550-10-3)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / tetrahydrofuran

2: TFA

3: NaHCO₃

With sodium hydrogencarbonate; triethylamine; trifluoroacetic acid; In tetrahydrofuran;

DOI:10.1021/ol025629g

upstream raw materials:

benzyl chloroformate

(2R,3R)-3-MeAzyOMe

(2R,3R)-1-trityl-3-methyl-2-aziridinecarboxylic acid methyl ester

N-trityl-D-threonine methyl ester

Downstream raw materials:

S-benzoyl-N-benzyloxycarbonyl-threo-3-methyl-D-cysteine methyl ester

(αR,βR)-N^α-carbobenzoxy-1,β-dimethyltryptophan

(2R,3R)-2-Benzyloxycarbonylamino-3-(1-ethyl-1H-indol-3-yl)-butyric acid

(2R,3R)-2-Benzyloxycarbonylamino-3-(1,5-dimethyl-1H-indol-3-yl)-butyric acid