(S,S)-N-(2-Benzyloxycarbonylisothiazolidine-1,1-dioxide-3-carbonyl)-phenylalanine methyl ester

Base Information

• Chemical Name: (S,S)-N-(2-Benzyloxycarbonylisothiazolidine-1,1-dioxide-3-carbonyl)-phenylalanine methyl ester
• CAS No.: 147878-96-4
• Molecular Formula: C₂₂H₂₄N₂O₇S
• Molecular Weight: 460.508
• Mol file: 147878-96-4.mol

Synonyms:(S,S)-N-(2-Benzyloxycarbonylisothiazolidine-1,1-dioxide-3-carbonyl)-phenylalanine methyl ester

Chemical Property of (S,S)-N-(2-Benzyloxycarbonylisothiazolidine-1,1-dioxide-3-carbonyl)-phenylalanine methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S,S)-N-(2-Benzyloxycarbonylisothiazolidine-1,1-dioxide-3-carbonyl)-phenylalanine methyl ester

There total 3 articles about (S,S)-N-(2-Benzyloxycarbonylisothiazolidine-1,1-dioxide-3-carbonyl)-phenylalanine 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: 66.0%

methyl (2S)-2-amino-3-phenylpropanoate (2577-90-4) + (S)-2-Benzyloxycarbonyl-isothiazolidine-1,1-dioxide-3-carboxylic acid (147878-95-3) → (S,S)-N-(2-Benzyloxycarbonylisothiazolidine-1,1-dioxide-3-carbonyl)-phenylalanine methyl ester (147878-96-4)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; 1) 5 h, 0 deg C, 2) 16 h, 5 deg C;

DOI:10.1002/ardp.19933260305

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (S,S)-N-(2-Benzyloxycarbonylisothiazolidine-1,1-dioxide-3-carbonyl)-phenylalanine methyl ester (147878-96-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 62 percent / N-methylmorpholine / CHCl₃ / 16 h / Heating

2: 90 percent / 0.1N NaOH / dioxane / 1.5 h / Ambient temperature

3: 66 percent / dicyclohexylcarbodiimide / CH₂Cl₂ / 1) 5 h, 0 deg C, 2) 16 h, 5 deg C

With 4-methyl-morpholine; sodium hydroxide; dicyclohexyl-carbodiimide; In 1,4-dioxane; dichloromethane; chloroform;

DOI:10.1002/ardp.19933260305

Reference yield:

(S)-2-Benzyloxycarbonyl-isothiazolidine-1,1-dioxide-3-carboxylic acid methyl ester (147878-94-2) → (S,S)-N-(2-Benzyloxycarbonylisothiazolidine-1,1-dioxide-3-carbonyl)-phenylalanine methyl ester (147878-96-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / 0.1N NaOH / dioxane / 1.5 h / Ambient temperature

2: 66 percent / dicyclohexylcarbodiimide / CH₂Cl₂ / 1) 5 h, 0 deg C, 2) 16 h, 5 deg C

With sodium hydroxide; dicyclohexyl-carbodiimide; In 1,4-dioxane; dichloromethane;

DOI:10.1002/ardp.19933260305

upstream raw materials:

methyl (2S)-2-amino-3-phenylpropanoate

(S)-2-Benzyloxycarbonyl-isothiazolidine-1,1-dioxide-3-carboxylic acid

benzyl chloroformate

(S)-2-Benzyloxycarbonyl-isothiazolidine-1,1-dioxide-3-carboxylic acid methyl ester