Z-L-histidine benzyl ester

Base Information

• Chemical Name: Z-L-histidine benzyl ester
• CAS No.: 20794-07-4
• Molecular Formula: C21H21 N3 O4
• Molecular Weight: 379.41
• Hs Code.: 2933290090
• DSSTox Substance ID: DTXSID90426715
• Wikidata: Q82239543
• Mol file: 20794-07-4.mol

Synonyms:Z-L-histidine benzyl ester;20794-07-4;Z-His-OBzl;benzyl (2S)-3-(1H-imidazol-5-yl)-2-(phenylmethoxycarbonylamino)propanoate;L-Histidine, N-[(phenylmethoxy)carbonyl]-, phenylmethyl ester;(S)-Benzyl 2-(((benzyloxy)carbonyl)amino)-3-(1H-imidazol-4-yl)propanoate;DTXSID90426715;MFCD03093505;NA-Z-L-HISTIDINE BENZYL ESTER;AKOS030241190;(S)-Benzyl2-(((benzyloxy)carbonyl)amino)-3-(1H-imidazol-4-yl)propanoate

Chemical Property of Z-L-histidine benzyl ester

Chemical Property:

• PSA: 96.80000
• LogP: 3.19500
• Storage Temp.: −20°C
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 379.15320616
• Heavy Atom Count: 28
• Complexity: 490

Purity/Quality:

98%Min ^*data from raw suppliers

(S)-Benzyl2-(((benzyloxy)carbonyl)amino)-3-(1H-imidazol-4-yl)propanoate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)C(CC2=CN=CN2)NC(=O)OCC3=CC=CC=C3
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)[C@H](CC2=CN=CN2)NC(=O)OCC3=CC=CC=C3

Technology Process of Z-L-histidine benzyl ester

There total 2 articles about Z-L-histidine benzyl 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: 63.0%

benzyl alcohol (100-51-6,185532-71-2) + N-[(benzyloxy)carbonyl]-L-histidine (14997-58-1) → Nα-(carbobenzyloxy)histidine benzyl ester (20794-07-4)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; Ambient temperature;

DOI:10.1021/jo961043u

Reference yield:

→ Nα-(carbobenzyloxy)histidine benzyl ester (20794-07-4)

Guidance literature:

L-Histidinbenzylester-p-tosylat, N-Benzyloxycarbonyloxy-succinimid (DMF, Triethylamin) (S.3540);

DOI:10.1002/cber.19681011026

Reference yield: 57.0%

Nα-(carbobenzyloxy)histidine benzyl ester (20794-07-4) + benzyl 4R,3-Benzyl-2,2-dioxo-1,2,3-oxathiazolidine-4-carboxylate (1311981-46-0) → dibenzyl Nα-tert-carbobenzyloxy-Nα'-benzyl-τ-L-histidino-D-alaninate (1311981-49-3)

Guidance literature:

N^α-(carbobenzyloxy)histidine benzyl ester; benzyl 4R,3-Benzyl-2,2-dioxo-1,2,3-oxathiazolidine-4-carboxylate; In 1,2-dimethoxyethane; at 80 ℃; for 5h;

With potassium dihydrogenphosphate; water; at 20 ℃;

DOI:10.1021/jo200744d

upstream raw materials:

benzyl alcohol

N-[(benzyloxy)carbonyl]-L-histidine

Downstream raw materials:

dibenzyl Nα-tert-carbobenzyloxy-Nα'-benzyl-τ-L-histidino-D-alaninate