(2S,3R)-2-Allyl-3-benzyloxycarbonylamino-succinic acid 1-methyl ester

Base Information

• Chemical Name: (2S,3R)-2-Allyl-3-benzyloxycarbonylamino-succinic acid 1-methyl ester
• CAS No.: 177288-60-7
• Molecular Formula: C₁₆H₁₉NO₆
• Molecular Weight: 321.33
• Mol file: 177288-60-7.mol

Synonyms:(2S,3R)-2-Allyl-3-benzyloxycarbonylamino-succinic acid 1-methyl ester

Chemical Property of (2S,3R)-2-Allyl-3-benzyloxycarbonylamino-succinic acid 1-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-2-Allyl-3-benzyloxycarbonylamino-succinic acid 1-methyl ester

There total 2 articles about (2S,3R)-2-Allyl-3-benzyloxycarbonylamino-succinic acid 1-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: 89.0%

tert-butyl (2S,3R)-2-(benzyloxycarbonylamino)-3-carbomethoxyhex-5-enoate (123975-54-2) → (2S,3R)-2-Allyl-3-benzyloxycarbonylamino-succinic acid 1-methyl ester (177288-60-7)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; a) -8 deg C, 70 h, b) from -8 deg C to 15 deg C, 24 h;

DOI:10.1021/jm9601009

Reference yield:

β-Methyl α-tert-butyl (2S)-N-(benzyloxycarbonyl)aspartate (60079-12-1) → (2S,3R)-2-Allyl-3-benzyloxycarbonylamino-succinic acid 1-methyl ester (177288-60-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) lithium hexamethyldisilazide / 1.) THF, hexane, -35 deg C, 150 min, 2.) THF, hexane, -75 deg C, 18 h

2: 89 percent / TFA / CH₂Cl₂ / a) -8 deg C, 70 h, b) from -8 deg C to 15 deg C, 24 h

With trifluoroacetic acid; lithium hexamethyldisilazane; In dichloromethane;

DOI:10.1021/jm9601009

Reference yield: 78.0%

(2S,3R)-2-Allyl-3-benzyloxycarbonylamino-succinic acid 1-methyl ester (177288-60-7) → (2S,3R,5R)-1-(benzyloxycarbonyl)-5-(hydroxymethyl)-3-(methoxycarbonyl)pyrrolidine-2-carboxylic acid (1032591-55-1)

Guidance literature:

With pyridine N-oxide; trifluoroacetic acid; citric acid; potassium dioxotetrahydroxoosmate(VI); In water; acetone; at 40 ℃; for 26h;

DOI:10.1002/anie.200705425

upstream raw materials:

tert-butyl (2S,3R)-2-(benzyloxycarbonylamino)-3-carbomethoxyhex-5-enoate

β-Methyl α-tert-butyl (2S)-N-(benzyloxycarbonyl)aspartate

Downstream raw materials:

(2S,3R,5R)-1-(benzyloxycarbonyl)-5-(hydroxymethyl)-3-(methoxycarbonyl)pyrrolidine-2-carboxylic acid