N-Boc-N'-benzyloxymethyl-L-histidine

Base Information

• Chemical Name: N-Boc-N'-benzyloxymethyl-L-histidine
• CAS No.: 79950-65-5
• Molecular Formula: C19H25 N3 O5
• Molecular Weight: 375.425
• European Community (EC) Number: 692-757-4
• Mol file: 79950-65-5.mol

Synonyms:N-(tert-Butoxy)carbonyl-N'-benzyloxymethyl-L-histidine; Boc-His(Bom)-OH

Chemical Property of N-Boc-N'-benzyloxymethyl-L-histidine

Chemical Property:

• Vapor Pressure: 5.11E-15mmHg at 25°C
• Melting Point: 122-125 ºC
• Boiling Point: 595.3oC at 760 mmHg
• PKA: 3.55±0.10(Predicted)
• Flash Point: 313.8oC
• PSA: 102.68000
• Density: 1.21g/cm3
• LogP: 2.96870
• Storage Temp.: 2-8°C
• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 375.17942091
• Heavy Atom Count: 27
• Complexity: 488

Purity/Quality:

99% ^*data from raw suppliers

Boc-His(Bom)-OH 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CN=CN1COCC2=CC=CC=C2)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC1=CN=CN1COCC2=CC=CC=C2)C(=O)O
• Uses: Boc-L-His(Bom)-OH, is an amino acid building block used in peptide synthesis. With a growing peptide drug market the fast, reliable synthesis of peptides is of great importance.

Technology Process of N-Boc-N'-benzyloxymethyl-L-histidine

There total 6 articles about N-Boc-N'-benzyloxymethyl-L-histidine 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: 87.0%

N(α)-t-butoxycarbonyl-N(?)-benzyloxymethyl-L-histidine methyl ester hydrochloride (83468-80-8) → N-[(1,1-dimethylethoxy)carbonyl]-3-[(phenylmethoxy)methyl]-L-histidine (79950-65-5,99310-01-7)

Guidance literature:

With sodium hydroxide; In methanol; for 0.25h;

Reference yield: 78.0%

Nα-tert-Boc-N?-<(benzyloxy)methyl>-L-histidine methyl ester (79950-77-9) → N-[(1,1-dimethylethoxy)carbonyl]-3-[(phenylmethoxy)methyl]-L-histidine (79950-65-5,99310-01-7)

Guidance literature:

With sodium hydroxide;

DOI:10.1039/c39810000648

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → N-[(1,1-dimethylethoxy)carbonyl]-3-[(phenylmethoxy)methyl]-L-histidine (79950-65-5,99310-01-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / Et₃N / methanol

2: 69 percent / CH₂Cl₂

3: 87 percent / aq. NaOH / methanol / 0.25 h

With sodium hydroxide; triethylamine; In methanol; dichloromethane;

upstream raw materials:

N^α-tert-Boc-N^?-<(benzyloxy)methyl>-L-histidine methyl ester

N(α)-t-butoxycarbonyl-N(?)-benzyloxymethyl-L-histidine methyl ester hydrochloride

di-tert-butyl dicarbonate

l-histidine methyl ester dihydrochloride

Downstream raw materials:

5-<1-Hydroxy-2(S)-<(tert-butyloxycarbonyl)amino>-3-<3-(benzyloxymethyl)imidazol-4-yl>propylidene>-2,2-dimethyl-1,3-dioxane-4,6-dione

L-histidyl-L-histidine

t-butoxycarbonylglycyl-N(?)-benzyloxymethyl-L-histidyl-L-phenylalanine methyl ester

N(α)-t-butoxycarbonyl-N(?)-benzyloxymethyl-L-histidyl-N(?)-benzyloxymethyl-L-histidine methyl ester

Refernces

• 1、 -. "N-HETEROCYCLIC ALCOHOL DERIVATIVES". . . Retrieved 2008/06/13.
• 2、 Brown, Tom,Jones, John H.,Richards, John D.. "Further Studies on the Protection of Histidine Side Chains in Peptide Synthesis: The Use of the ?-Benzyloxymethyl Group". . p. 1553 - 1562. Retrieved 2007/10/02.