Boc-Tyr-OtBu

Base Information

• Chemical Name: Boc-Tyr-OtBu
• CAS No.: 18938-60-8
• Molecular Formula: C18H27NO5
• Molecular Weight: 337.416
• Mol file: 18938-60-8.mol

Synonyms:L-tyrosine-N-Boc-tert-butyl ester;N-Boc-L-tyrosine tert-butyl ester;N-α-Boc-L-tyrosine t-butyl ester;(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionic acid tert-butyl ester;(S)-tert-butyl 2-((tert-butoxycarbonyl)amino)-3-(4-hydroxyphenyl) propanoate;N-Boc-L-tyrosine t-butyl ester;(S)-(+)-2-tert-butoxycarbonylamino-3-(4-hydroxyphenyl)propionic acid tert-butyl ester;L-Tyrosine, N-[(1,1-dimethylethoxy)carbonyl]-, 1,1-dimethylethyl ester;Boc-Tyr-OtBu;

Chemical Property of Boc-Tyr-OtBu

Chemical Property:

• Melting Point: 111-112 °C(Solv: ligroine (8032-32-4); ethyl acetate (141-78-6))
• Boiling Point: 476.0±40.0 °C(Predicted)
• PKA: 9.75±0.15(Predicted)
• PSA: 84.86000
• Density: 1.117±0.06 g/cm3(Predicted)
• LogP: 3.56060
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

Boc-Tyr-OtBu 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Boc-Tyr-OtBu

There total 12 articles about Boc-Tyr-OtBu 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: 100.0%

di-tert-butyl dicarbonate (24424-99-5) + Tyr(tBu) (16874-12-7,87553-74-0) → (S)-tert-butyl 2-((tert-butoxycarbonyl)amino)-3-(4-hydroxyphenyl)propanoate (18938-60-8)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/acs.joc.9b02548

Reference yield: 92.0%

t-butyl bromide (507-19-7) + Boc-Tyr-OH (3978-80-1) → (S)-tert-butyl 2-((tert-butoxycarbonyl)amino)-3-(4-hydroxyphenyl)propanoate (18938-60-8)

Guidance literature:

With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate; In N,N-dimethyl acetamide; at 55 ℃; for 48h; Inert atmosphere;

DOI:10.1002/chem.201202474

Reference yield: 88.5%

di-tert-butyl dicarbonate (24424-99-5) + tert-butyl (2S)-2-amino-3-(4-hydroxyphenyl)propanoate hydrogen chloride → (S)-tert-butyl 2-((tert-butoxycarbonyl)amino)-3-(4-hydroxyphenyl)propanoate (18938-60-8)

Guidance literature:

With sodium hydrogencarbonate; In water; acetone; at 20 - 25 ℃; for 2h; Large scale;

upstream raw materials:

N-(tert-butyloxycarbonyl) azide

Tyr(tBu)

tert-Butyl 2,2,2-trichloroacetimidate

Boc-Tyr-OH

Downstream raw materials:

Boc-Tyr-OH

tert-butyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-(((trifluoromethyl)sulfonyl)oxy)phenyl)propanoate

(S)-(+)-6-(4-(2-[4-(2-tert-butoxycarbonyl-2-tert-butoxycarbonylaminoethyl)phenoxy]ethoxysulfonyl)phenyl)hexanoic acid methyl ester

(S)-(+)-6-(4-[2-[4-(2-tert-butoxycarbonyl-2-tert-butoxycarbonylaminoethyl)phenoxy]ethoxysulfonyl]phenyl)hexanoic acid

Refernces

• 1、 He, Chunmao,Li, Changpeng. "Facile synthesis of sulfotyrosine-containing α-conotoxins". supporting information. p. 7559 - 7564. Retrieved 2020/10/14.
• 2、 Maisonial-Besset, Aurélie,Serre, Audrey,Ouadi, Ali,Schmitt, Sébastien,Canitrot, Damien,Léal, Fernand,Miot-Noirault, Elisabeth,Brasse, David,Marchand, Patrice,Chezal, Jean-Michel. "Base/Cryptand/Metal-Free Automated Nucleophilic Radiofluorination of [18F]FDOPA from Iodonium Salts: Importance of Hydrogen Carbonate Counterion". supporting information. p. 7058 - 7065. Retrieved 2019/01/04.