BOC-L-TYR(ALL)-OH

Base Information

• Chemical Name: BOC-L-TYR(ALL)-OH
• CAS No.: 127132-38-1
• Molecular Formula: C17H23NO5
• Molecular Weight: 321.373
• Hs Code.: 2924299090
• Mol file: 127132-38-1.mol

Synonyms:L-Tyrosine,N-[(1,1-dimethylethoxy)carbonyl]-O-2-propenyl- (9CI);

Chemical Property of BOC-L-TYR(ALL)-OH

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.526
• Boiling Point: 490.39 °C at 760 mmHg
• Flash Point: 250.379 °C
• PSA: 84.86000
• Density: 1.145 g/cm³
• LogP: 3.16270
• Storage Temp.: 2-8°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

Boc-O-allyl-L-tyrosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Due to gem-dimethyl substituent effect, Boc-Tyr(Allyl)-OH is found to be resistant to Claisen rearrangement in water.

Technology Process of BOC-L-TYR(ALL)-OH

There total 12 articles about BOC-L-TYR(ALL)-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: 99.0%

(S)-Ethyl 3-(4-(allyloxy)phenyl)-2-((tert-butoxycarbonyl)amino) propanoate (127132-37-0) → N-(tert-butyloxycarbonyl)-O-allyl-(S)-tyrosine (127132-38-1)

Guidance literature:

With sodium hydroxide; In ethanol; Ambient temperature;

DOI:10.1021/jm00168a015

Reference yield: 98.0%

methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-[4-(prop-2-en-1-yloxy)phenyl]-propanoate (147363-23-3) → N-(tert-butyloxycarbonyl)-O-allyl-(S)-tyrosine (127132-38-1)

Guidance literature:

With methanol; sodium hydroxide; at 20 ℃;

DOI:10.1016/j.bmc.2015.04.060

Reference yield: 86.0%

(S)-3-(4-Allyloxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid allyl ester (156945-63-0) → N-(tert-butyloxycarbonyl)-O-allyl-(S)-tyrosine (127132-38-1)

Guidance literature:

With sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)73351-X

upstream raw materials:

(S)-Ethyl 3-(4-(allyloxy)phenyl)-2-((tert-butoxycarbonyl)amino) propanoate

Boc-Tyr-OH

allyl bromide

(S)-3-(4-Allyloxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid allyl ester

Downstream raw materials:

(S)-2-[(S)-3-(4-allyloxy-phenyl)-2-tert-butoxycarbonylamino-propionylamino]-3-methyl-butyric acid methyl ester

Boc-Tyr-OH

{4-[3-(4-allyloxy-phenyl)-2-amino-propionyl]-3-methoxycarbonylmethyl-2-oxo-piperazin-1-yl}-acetic acid

N-(tert-butoxycarbonyl)-L-valyl-O'-(prop-2-enyl)-L-tyrosyl-L-valine methyl ester

Refernces

• 1、 Tran Van, Chien,Nennstiel, Dirk,Scherkenbeck, Jürgen. "Macrocyclic analogues of the diuretic insect neuropeptide helicokinin I show strong receptor-binding". . p. 3278 - 3286. Retrieved 2015.
• 2、 Kim, Hyun J.,Jackson, W. Roy. "Polymer Attached Cyclic Dipeptides as Catalysts for Enantioselective Cyanohydrin Formation". . p. 1421 - 1430. Retrieved 1992.
• 3、 Akagi, Ken-ichi,Masuda, Yuichi,Monobe, Yoko,Shibata, Kana,Tanaka, Fumiya. "Design and synthesis of β-strand-fixed peptides inhibiting aggregation of amyloid β-protein". supporting information. . Retrieved 2020/08/07.