5-tert-Butyl 1-(2,5-dioxopyrrolidin-1-yl) (S)-2-(((phenylmethoxy)carbonyl)amino)glutarate

Base Information

• Chemical Name: 5-tert-Butyl 1-(2,5-dioxopyrrolidin-1-yl) (S)-2-(((phenylmethoxy)carbonyl)amino)glutarate
• CAS No.: 4666-16-4
• Molecular Formula: C21H26N2O8
• Molecular Weight: 434.446
• European Community (EC) Number: 225-111-3
• DSSTox Substance ID: DTXSID60196897
• Nikkaji Number: J297.877F
• Wikidata: Q76009933
• Mol file: 4666-16-4.mol

Synonyms:Z-Glu(OtBu)-OSu;4666-16-4;EINECS 225-111-3;5-O-tert-butyl 1-O-(2,5-dioxopyrrolidin-1-yl) (2S)-2-(phenylmethoxycarbonylamino)pentanedioate;5-tert-Butyl 1-(2,5-dioxopyrrolidin-1-yl) (S)-2-(((phenylmethoxy)carbonyl)amino)glutarate;(S)-5-tert-Butyl 1-(2,5-dioxopyrrolidin-1-yl) 2-(((benzyloxy)carbonyl)amino)pentanedioate;Cbz-L-glutamic acid 5-tert-butyl-1-(N-succinimidyl) ester;5-tert-butyl 1-(2,5-dioxopyrrolidin-1-yl) (S)-2-[[(phenylmethoxy)carbonyl]amino]glutarate;Z-Glu(OBut)-Osu;Z-L-Glu(OtBu)-OSu;SCHEMBL2777934;DTXSID60196897;MFCD00153329;AKOS027327993;FD21459;AS-49078;CS-0204655;(S)-5-tert-butyl 1-(2,5-dioxopyrrolidin-1-yl) 2-(benzyloxycarbonylamino)pentanedioate;(S)-5-tert-Butyl1-(2,5-dioxopyrrolidin-1-yl)2-(((benzyloxy)carbonyl)amino)pentanedioate;N-Benzyloxycarbonyl-L-glutamic acid 5-tert-butyl ester N-succinimidyl ester, 95%;(S)-5-[(2,5-Dioxopyrrolidin-1-yl)oxy]-5-oxo-4-[[(benzyloxy)carbonyl]amino]pentanoic acid tert-butyl ester;N-alpha-BenZyloxycarbonyl-L-glutamic acid alpha-succinimidyl gamma-t-butyl ester (CbZ-L-Glu(tBu)-OSu)

Chemical Property of 5-tert-Butyl 1-(2,5-dioxopyrrolidin-1-yl) (S)-2-(((phenylmethoxy)carbonyl)amino)glutarate

Chemical Property:

• Melting Point: 105-107 °C
• Refractive Index: 1.556
• PSA: 128.31000
• Density: 1.29 g/cm³
• LogP: 2.33930
• Storage Temp.: −20°C
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 12
• Exact Mass: 434.16891579
• Heavy Atom Count: 31
• Complexity: 678

Purity/Quality:

99% ^*data from raw suppliers

Z-Glu(otbu)-osu ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)CCC(C(=O)ON1C(=O)CCC1=O)NC(=O)OCC2=CC=CC=C2
• Isomeric SMILES: CC(C)(C)OC(=O)CC[C@@H](C(=O)ON1C(=O)CCC1=O)NC(=O)OCC2=CC=CC=C2

Technology Process of 5-tert-Butyl 1-(2,5-dioxopyrrolidin-1-yl) (S)-2-(((phenylmethoxy)carbonyl)amino)glutarate

There total 2 articles about 5-tert-Butyl 1-(2,5-dioxopyrrolidin-1-yl) (S)-2-(((phenylmethoxy)carbonyl)amino)glutarate 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: 93.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 5-tert-butyl N-benzyloxycarbonyl-L-glutamate (3886-08-6) → 5-tert-butyl 1-(2,5-dioxopyrrolidin-1-yl) (S)-2-{[(phenylmethoxy)carbonyl]amino}glutarate (4666-16-4)

Guidance literature:

With dicyclohexyl-carbodiimide; In ethyl acetate; at 10 - 20 ℃; for 21h;

DOI:10.1007/s11094-020-02168-0

Reference yield:

→ 5-tert-butyl 1-(2,5-dioxopyrrolidin-1-yl) (S)-2-{[(phenylmethoxy)carbonyl]amino}glutarate (4666-16-4)

Guidance literature:

Z-(Glu-O-t-Bu)-OH, N-Hydroxysuccinimid;

Reference yield: 95.0%

5-tert-butyl 1-(2,5-dioxopyrrolidin-1-yl) (S)-2-{[(phenylmethoxy)carbonyl]amino}glutarate (4666-16-4) + C28H56N6O8 → C62H98N8O18

Guidance literature:

In N,N-dimethyl-formamide; at 20 ℃; for 24h;

DOI:10.1007/s11094-020-02168-0

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

5-tert-butyl N-benzyloxycarbonyl-L-glutamate

Downstream raw materials:

Z-Glu(OtBu)-Glu(OtBu)

Z-Glu(OBu^t)-Gly-OBzl

N^α-Benzyloxycarbonyl-γ-tert.-butyl-Glu-Gly

Benzyloxycarbonyl-α-L-glutamyl(γ-tert-butyl ester)-valinol

Refernces

• 1、 Jadhav, Sandip V.,Misra, Rajkumar,Singh, Sumeet K.,Gopi, Hosahudya N.. "Efficient access to enantiopure γ4-amino acids with proteinogenic side-chains and structural investigation of γ4- asn and γ4-ser in hybrid peptide helices". supporting information. p. 16256 - 16262. Retrieved 2013/12/04.