Boc-His-OH

Base Information

• Chemical Name: Boc-His-OH
• CAS No.: 17791-52-5
• Molecular Formula: C11H17N3O4
• Molecular Weight: 255.274
• Hs Code.: 29339900
• European Community (EC) Number: 241-768-9
• DSSTox Substance ID: DTXSID80170396
• Nikkaji Number: J26.591H
• Wikidata: Q72449492
• ChEMBL ID: CHEMBL1222274
• Mol file: 17791-52-5.mol

Synonyms:Boc-His;tert-butyloxycarbonyl-L-histidine

Chemical Property of Boc-His-OH

Chemical Property:

• Appearance/Colour: white fine powder
• Vapor Pressure: 9.89E-12mmHg at 25°C
• Melting Point: 195 °C (dec.)(lit.)
• Refractive Index: 26 ° (C=1, MeOH)
• Boiling Point: 522.2 °C at 760 mmHg
• PKA: 3.56±0.10(Predicted)
• Flash Point: 269.6 °C
• PSA: 104.31000
• Density: 1.275 g/cm³
• LogP: 1.32100
• Storage Temp.: -20°C
• Solubility.: DMSO (Slightly), Methanol (Sparingly, Heated)
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 255.12190603
• Heavy Atom Count: 18
• Complexity: 314

Purity/Quality:

99% ^*data from raw suppliers

Nα-Boc-L-histidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CN=CN1)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC1=CN=CN1)C(=O)O
• Uses: Nα-Boc-L-histidine is an N-Boc-protected form of L-Histidine (H456010). L-Histidine is an essential amino acid that plays an important role in mitochondrial glutamine transport and has potential of abolishing oxidative stress caused by brain edema.L-Histidine promotes zinc uptake in human erythrocyes and also has potential as an antioxidant therapy for acute mammary inflammation in cattle.

Technology Process of Boc-His-OH

There total 18 articles about Boc-His-OH 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: 92.0%

di-tert-butyl dicarbonate (24424-99-5) + L-histidine (71-00-1) → N-(tert-butoxycarbonyl)-L-histidine (17791-52-5)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; at 20 ℃; for 12h;

DOI:10.1039/d1ob00798j

Reference yield: 89.0%

N(α)-t-butoxycarbonyl-N(?)-benzyloxymethyl-L-histidine (83468-83-1) → N-(tert-butoxycarbonyl)-L-histidine (17791-52-5)

Guidance literature:

With magnesium; hydrazinium monoformate; In methanol; at 25 ℃; for 2h;

DOI:10.1016/S0040-4039(01)02113-X

Reference yield: 88.0%

Boc-His(Z) (50305-43-6) → N-(tert-butoxycarbonyl)-L-histidine (17791-52-5)

Guidance literature:

With magnesium; hydrazinium monoformate; In methanol; at 25 ℃; for 1h;

DOI:10.1016/S0040-4039(01)02113-X

upstream raw materials:

L-histidine hydrochloride monohydrate

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

(S)-2-tert-Butoxycarbonylamino-3-[1-(4-methoxy-2,3,6-trimethyl-benzenesulfonyl)-1H-imidazol-4-yl]-propionic acid; compound with dicyclohexyl-amine

N,1'-bis[(1,1-dimethylethoxy)carbonyl]-L-histidine

Downstream raw materials:

1,Ile⁸>angiotensin II

1,Tyr(Me)⁴,Ile⁸>angiotensin II

1,Tyr(Me)⁴>angiotensin II

N-α-(tert-butoxycarbonyl)-τ-isopropyl-L-histidine

Refernces

• 1、 Flouret,Morgan,Gendrich,Wilber,Seibel. "Synthesis of the thyrotropin releasing hormone enantiomer and some diastereoisomers and in vitro studies of their biological activity". . p. 1137 - 1140. Retrieved 1973.
• 2、 Li, Tingting,Xu, Bo. "Mechanically Strong Heterogeneous Catalysts via Immobilization of Powderous Catalysts to Porous Plastic Tablets". supporting information. p. 2673 - 2678. Retrieved 2021/08/03.
• 3、 Zhou, Mi,Li, Tingting,Xu, Bo. "Easy-handling and low-leaching heterogeneous palladium and platinum catalysts via coating with a silicone elastomer". supporting information. p. 948 - 952. Retrieved 2019/03/08.