Z-Pyr-OtBu

Base Information

• Chemical Name: Z-Pyr-OtBu
• CAS No.: 81470-51-1
• Molecular Formula: C17H21NO5
• Molecular Weight: 319.357
• European Community (EC) Number: 899-192-4
• Nikkaji Number: J461.876I
• Mol file: 81470-51-1.mol

Synonyms:Z-Pyr-OtBu;81470-51-1;1-O-benzyl 2-O-tert-butyl (2S)-5-oxopyrrolidine-1,2-dicarboxylate;SCHEMBL7420306;VLWCTEHZKXFOHR-ZDUSSCGKSA-N;MFCD11975830;AKOS025289494;DS-7562;CS-0154860;D97600;1-Benzyl 2-tert-butyl (S)-5-oxo-1,2-pyrrolidinedicarboxylate;(S)-1-BENZYL 2-TERT-BUTYL 5-OXOPYRROLIDINE-1,2-DICARBOXYLATE

Chemical Property of Z-Pyr-OtBu

Chemical Property:

• PSA: 72.91000
• LogP: 2.59380
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 319.14197277
• Heavy Atom Count: 23
• Complexity: 462

Purity/Quality:

98.5% ^*data from raw suppliers

Z-Pyr-OtBu ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C1CCC(=O)N1C(=O)OCC2=CC=CC=C2
• Isomeric SMILES: CC(C)(C)OC(=O)[C@@H]1CCC(=O)N1C(=O)OCC2=CC=CC=C2

Technology Process of Z-Pyr-OtBu

There total 16 articles about Z-Pyr-OtBu 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: 90.0%

L-t-butyl pyroglutamate (35418-16-7,85136-12-5) + benzyl chloroformate (501-53-1,94274-21-2) → tert-butyl N-benzyloxycarbonyl-L-pyroglutamate (81470-51-1)

Guidance literature:

L-t-butyl pyroglutamate; With sodium hydride; In tetrahydrofuran; mineral oil; at 20 ℃; for 0.5h; Inert atmosphere;

benzyl chloroformate; In tetrahydrofuran; mineral oil; at 20 ℃; for 20h; Inert atmosphere;

DOI:10.1021/ol5023195

Reference yield: 85.0%

L-t-butyl pyroglutamate (35418-16-7,85136-12-5) + dibenzyl dicarbonate (31139-36-3) → tert-butyl N-benzyloxycarbonyl-L-pyroglutamate (81470-51-1)

Guidance literature:

With dmap; In acetonitrile; at 20 ℃; for 3h;

DOI:10.1080/00304940109356611

Reference yield: 81.0%

(S)-2-tert-butyl-1-benzylpyrrolidine-1,2-dicarboxylate (16881-39-3) → tert-butyl N-benzyloxycarbonyl-L-pyroglutamate (81470-51-1)

Guidance literature:

With methanesulfonic acid; 9-azabicyclo[3.3.1]nonan-3-one N-oxyl oxide; water; lithium perchlorate; In acetonitrile; at 25 ℃; Reagent/catalyst; Catalytic behavior; Electrolysis;

DOI:10.1021/acs.orglett.1c03338

upstream raw materials:

acetic acid tert-butyl ester

Cbz-L-pGlu-OH

1-tert-butyl 5-methyl (2S)-2-{[(benzyloxy)carbonyl]amino}pentanedioate

L-glutamic acid

Downstream raw materials:

benzyloxycarbonyl-L-glutamic acid α-tert-butyl ester γ-hydrazide

tert-butyl (2S)-1-(benzyloxycarbonyl)-4α-(phenylmethyl)pyroglutamate

tert-butyl (2S)-1-(benzyloxycarbonyl)-4α-(hydroxy(p-fluoroohenyl)methyl)pyroglutamate

tert-butyl (2S)-1-(benzyloxycarbonyl)-4β-(hydroxy(p-fluoroohenyl)methyl)pyroglutamate

Refernces

• 1、 Kazmierski, Wieslaw M.,Miriyala, Nagaraju,Johnson, David K.,Baskaran, Sam. "The Discovery of Conformationally Constrained Bicyclic Peptidomimetics as Potent Hepatitis C NS5A Inhibitors". supporting information. p. 1649 - 1655. Retrieved 2021/10/04.
• 2、 -. "PREPARATION AND USES OF REACTIVE OXYGEN SPECIES SCAVENGER DERIVATIVES". Page/Page column 99-100. . Retrieved 2019/03/07.