Boc-His(Tos)-OH

Base Information

• Chemical Name: Boc-His(Tos)-OH
• CAS No.: 35899-43-5
• Molecular Formula: C18H23N3O6S
• Molecular Weight: 409.463
• Hs Code.: 29350090
• DSSTox Substance ID: DTXSID50424176
• Nikkaji Number: J26.566G
• Wikidata: Q72449497
• Mol file: 35899-43-5.mol

Synonyms:Boc-His(Tos)-OH;35899-43-5;Boc-L-His(Tos)-OH;(R)-L-(+)-Boc-his(tos)-OH;(2S)-3-[1-(4-methylphenyl)sulfonylimidazol-4-yl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid;Boc-L-Histidine(Tosyl);Boc-His(1-Tos)-OH;(S)-2-((tert-Butoxycarbonyl)amino)-3-(1-tosyl-1H-imidazol-4-yl)propanoic acid;MFCD00065967;Boc-His-(Tos);Boc-His(-Tos)-OH;SCHEMBL3912355;DTXSID50424176;DCLJSEPKYJSEHW-HNNXBMFYSA-N;Nalpha-Boc-tele-tosyl-L-histidine;(S)-2-(tert-butoxycarbonylamino)-3-(1-tosyl-1H-imidazol-4-yl)propanoic acid;AKOS015924156;CS-W013863;FD21680;HY-W013147;n(Alpha)-boc-n(im)-tosyl-L-histidine;AS-12312;Boc-His(Tos)-OH, >=98.0% (TLC);B2066;M03290;A823029;J-300150;Q-101827;Nalpha-(tert-Butoxycarbonyl)-tele-(p-toluenesulfonyl)-L-histidine;N-alpha-t-Butyloxycarbonyl-N-im-tosyl-L-histidine (Boc-L-His(Tos)-OH);L-Histidine,N-[(1,1-dimethylethoxy)carbonyl]-1-[(4-methylphenyl)sulfonyl]-;(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-[1-(4-methylbenzenesulfonyl)-1H-imidazol-4-yl]propanoic acid

Chemical Property of Boc-His(Tos)-OH

Chemical Property:

• Appearance/Colour: White to light yellow crystal powder
• Melting Point: ~125 °C (dec.)
• Refractive Index: 1.594
• PKA: 3.50±0.10(Predicted)
• PSA: 135.97000
• Density: 1.33 g/cm³
• LogP: 3.42060
• Storage Temp.: −20°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 8
• Exact Mass: 409.13075664
• Heavy Atom Count: 28
• Complexity: 662

Purity/Quality:

99% ^*data from raw suppliers

Nalpha-(tert-Butoxycarbonyl)-tele-(p-toluenesulfonyl)-L-histidine >98.0%(T) ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)N2C=C(N=C2)CC(C(=O)O)NC(=O)OC(C)(C)C
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)N2C=C(N=C2)C[C@@H](C(=O)O)NC(=O)OC(C)(C)C
• Uses: Boc-L-His(Tos)-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 Boc-His(Tos)-OH

There total 2 articles about Boc-His(Tos)-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: 46.0%

p-toluenesulfonyl chloride (98-59-9) + N-(tert-butoxycarbonyl)-L-histidine (17791-52-5) → Boc-His(Tos)-OH (35899-43-5)

Guidance literature:

With sodium carbonate; In water; for 4h; Ambient temperature;

DOI:10.1021/jm00069a001

Reference yield:

→ Boc-His(Tos)-OH (35899-43-5)

Guidance literature:

Boc-His(Boc)-OMe (III-b) 1)NaOH 2)Tosylchlorid;

DOI:10.1246/bcsj.47.3146

Reference yield: 100.0%

Boc-His(Tos)-OH (35899-43-5) → L-histidine (71-00-1)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; diphenyl sulfide; In trifluoroacetic acid; at 0 ℃; for 0.5h; Product distribution; New peptide deprotection procedure: hard-soft acid-base concept; the role of soft bases (thioanisole, dimethylsulfide, diphenylsulfide) employed.;

DOI:10.1248/cpb.35.3447

upstream raw materials:

p-toluenesulfonyl chloride

N-(tert-butoxycarbonyl)-L-histidine

Downstream raw materials:

Ac-His-Phe-NH₂

Boc-His(Tos)-ONB

H-His-Asp-Phe-Gly-Val-Gly-Leu-Met-NH2

Boc-Asp(Bzl)-His-Val-Arg(Tos)-Thr(Bzl)-Lys(Z)-Gly-OH

Refernces

• 1、 -. "Peptides related to somatostatin". . . Retrieved 2008/06/13.
• 2、 -. "Novel decapeptide amide analogs of leuteinizing hormone-releasing hormone". . . Retrieved 2008/06/13.