Boc-D-tyrosine

Base Information

• Chemical Name: Boc-D-tyrosine
• CAS No.: 3978-80-1
• Molecular Formula: C14H19NO5
• Molecular Weight: 281.309
• Hs Code.: 29242990
• European Community (EC) Number: 223-613-7
• Nikkaji Number: J577.232J
• Metabolomics Workbench ID: 130107
• ChEMBL ID: CHEMBL302367
• Mol file: 3978-80-1.mol

Synonyms:Boc-Tyr;tert-butoxycarbonyl-L-tyrosine;tert-butoxycarbonyl-tyrosine

Chemical Property of Boc-D-tyrosine

Chemical Property:

• Appearance/Colour: white to off-white powder
• Vapor Pressure: 3.23E-10mmHg at 25°C
• Melting Point: 133-135 °C(lit.)
• Refractive Index: 1.5230 (estimate)
• Boiling Point: 484.9 °C at 760 mmHg
• PKA: 2.98±0.10(Predicted)
• Flash Point: 247.1 °C
• PSA: 95.86000
• Density: 1.238 g/cm³
• LogP: 2.30350
• Storage Temp.: −20°C
• Solubility.: DMSO (Slightly), Methanol (Sparingly)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 281.12632271
• Heavy Atom Count: 20
• Complexity: 342

Purity/Quality:

99% ^*data from raw suppliers

Boc-Tyr-OH ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC=C(C=C1)O)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](CC1=CC=C(C=C1)O)C(=O)O
• Uses: N-Boc-L-tyrosine is an N-Boc-protected form of L-Tyrosine (T899975). L-Tyrosine is an essential amino acid that exhibits in vitro antioxidant and antiradical activities. L-Tyrosine is used as a precursor to synthesize catecholamines (e.g. Norepinephrine HCl [N674500]) in human keratinocytes, and also for the synthesis of proteins and thyroid hormones.

Technology Process of Boc-D-tyrosine

There total 34 articles about Boc-D-tyrosine 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: 95.0%

(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester (4326-36-7) → Boc-Tyr-OH (3978-80-1)

Guidance literature:

With sodium hydroxide; In methanol;

Reference yield: 93.0%

O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3,54784-43-9) → Boc-Tyr-OH (3978-80-1)

Guidance literature:

With hydrogen; In ethanol; for 0.75h;

DOI:10.1039/c0ob00962h

Reference yield: 92.0%

O-(tert-butyl) S-(pyridin-2-yl)carbonothioate (105678-24-8) + L-tyrosine, dicyclohexylammonium salt → 2-Sulfanylpyridine (2637-34-5,73018-10-7) + Boc-Tyr-OH (3978-80-1)

Guidance literature:

With triethylamine; In water; N,N-dimethyl-formamide; for 16h; Ambient temperature;

DOI:10.1246/bcsj.58.3570

upstream raw materials:

tert-Butyl 4-nitrophenyl carbonate

L-tyrosine

tert-butyl alcohol

N-tert-butoxycarbonyl-L-tyrosine benzyl ester

Downstream raw materials:

Boc-Tyr-OTcp

N-(tert-butoxycarbonyl)-L-tyrosine ethyl ester

Boc-Tyr-Ser-OMe

BOCTyrIleOH

Refernces

• 1、 Nishiyama,Ishizuka,Shikama,Kurita. "An efficient synthesis of N-tert-butoxycarbonyl-O-cyclohexyl-L-tyrosine". . p. 233 - 235. Retrieved 2001.
• 2、 Singh, Narendra,Singh, Ramesh,Sharma, Swati,Kesharwani, Khushboo,Joshi, Khashti Ballabh,Verma, Sandeep. "Transition-metal ion-mediated morphological transformation of pyridine-based peptide nanostructures". supporting information. p. 153 - 161. Retrieved 2021/01/11.
• 3、 Chen, Jason S.,Dik, David A.,Schultz, Peter G.,Webb, Bill,Zhang, Nan. "Semisynthesis of a Bacterium with Non-canonical Cell-Wall Cross-Links". supporting information. p. 10910 - 10913. Retrieved 2020/07/08.