Z-L-glutamic acid gamma-methyl ester alpha-N-hydroxysuccinimide ester

Base Information

• Chemical Name: Z-L-glutamic acid gamma-methyl ester alpha-N-hydroxysuccinimide ester
• CAS No.: 39538-31-3
• Molecular Formula: C18H20 N2 O8
• Molecular Weight: 392.36
• DSSTox Substance ID: DTXSID70436973
• Wikidata: Q82252328
• Mol file: 39538-31-3.mol

Synonyms:Z-L-glutamic acid gamma-methyl ester alpha-N-hydroxysuccinimide ester;1-O-(2,5-dioxopyrrolidin-1-yl) 5-O-ethyl (2S)-2-(phenoxycarbonylamino)pentanedioate;CTK8G3860;DTXSID70436973;AKOS030242063;(4-OXO-4H-QUINAZOLIN-3-YL)-ACETICACIDHYDRAZIDE

Chemical Property of Z-L-glutamic acid gamma-methyl ester alpha-N-hydroxysuccinimide ester

Chemical Property:

• PSA: 128.31000
• LogP: 1.17060
• Storage Temp.: -15°C
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 11
• Exact Mass: 392.12196560
• Heavy Atom Count: 28
• Complexity: 599

Purity/Quality:

99% ^*data from raw suppliers

Z-L-glutamic acid γ-methyl ester alpha-N-hydroxysuccinimide ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CCC(C(=O)ON1C(=O)CCC1=O)NC(=O)OC2=CC=CC=C2
• Isomeric SMILES: CCOC(=O)CC[C@@H](C(=O)ON1C(=O)CCC1=O)NC(=O)OC2=CC=CC=C2

Technology Process of Z-L-glutamic acid gamma-methyl ester alpha-N-hydroxysuccinimide ester

There total 3 articles about Z-L-glutamic acid gamma-methyl ester alpha-N-hydroxysuccinimide 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:

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + (S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-methyl ester (4652-65-7) → methyl (4S)-4-{[(benzyloxy)carbonyl]amino}-5-[(2,5-dioxo-1-pyrrolidinyl)oxy]-5-oxopentanoate (39538-31-3)

Guidance literature:

With dicyclohexyl-carbodiimide; In ethyl acetate; at 0 - 20 ℃;

DOI:10.1016/S0957-4166(98)00466-2

Reference yield:

L-glutamic acid 5-methyl ester (1499-55-4) → methyl (4S)-4-{[(benzyloxy)carbonyl]amino}-5-[(2,5-dioxo-1-pyrrolidinyl)oxy]-5-oxopentanoate (39538-31-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / aq. Na₂CO₃ / dioxane / Ambient temperature

2: DCC / ethyl acetate / 0 - 20 °C

With sodium carbonate; dicyclohexyl-carbodiimide; In 1,4-dioxane; ethyl acetate;

DOI:10.1016/S0957-4166(98)00466-2

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → methyl (4S)-4-{[(benzyloxy)carbonyl]amino}-5-[(2,5-dioxo-1-pyrrolidinyl)oxy]-5-oxopentanoate (39538-31-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / aq. Na₂CO₃ / dioxane / Ambient temperature

2: DCC / ethyl acetate / 0 - 20 °C

With sodium carbonate; dicyclohexyl-carbodiimide; In 1,4-dioxane; ethyl acetate;

DOI:10.1016/S0957-4166(98)00466-2

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

(S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-methyl ester

L-glutamic acid 5-methyl ester

benzyl chloroformate

Downstream raw materials:

(S)-2,2-Dimethyl-4-(4-oxo-3-phenoxy-cyclohex-2-enylmethyl)-oxazolidine-3-carboxylic acid benzyl ester

(4S)-3-(benzyloxycarbonyl)-2,2-dimethyl-4-(methoxycarbonylethyl)oxazolidine

(4S)-3-(benzyloxycarbonyl)-2,2-dimethyl-4-(3-oxo-propyl)oxazolidine

4-(S)-[4-(N-benzyloxycarbonylamino)-5-hydroxy]pentanoic acid methyl ester

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