N-{[(Prop-2-en-1-yl)oxy]carbonyl}-L-phenylalanine

Base Information

• Chemical Name: N-{[(Prop-2-en-1-yl)oxy]carbonyl}-L-phenylalanine
• CAS No.: 90508-20-6
• Molecular Formula: C13H15NO4
• Molecular Weight: 249.266
• DSSTox Substance ID: DTXSID60553446
• Nikkaji Number: J834.278D
• Wikidata: Q82434030
• Mol file: 90508-20-6.mol

Synonyms:90508-20-6;((Allyloxy)carbonyl)-L-phenylalanine;N-{[(Prop-2-en-1-yl)oxy]carbonyl}-L-phenylalanine;(2S)-3-phenyl-2-(prop-2-enoxycarbonylamino)propanoic acid;L-Phenylalanine, N-[(2-propenyloxy)carbonyl]-;(S)-2-(((Allyloxy)carbonyl)amino)-3-phenylpropanoic acid;(2S)-3-phenyl-2-{[(prop-2-en-1-yloxy)carbonyl]amino}propanoic acid;Alloc-Phe-OH;starbld0019573;SCHEMBL2966988;N-(allyloxycarbonyl)phenylalanine;DTXSID60553446;FVBZCQLQINXRAC-NSHDSACASA-N;MFCD02094423;AKOS010379183;HY-W049168;CS-0101936;D76252;EN300-14983637

Chemical Property of N-{[(Prop-2-en-1-yl)oxy]carbonyl}-L-phenylalanine

Chemical Property:

• PSA: 79.12000
• LogP: 1.79890
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 249.10010796
• Heavy Atom Count: 18
• Complexity: 297

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CCOC(=O)NC(CC1=CC=CC=C1)C(=O)O
• Isomeric SMILES: C=CCOC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O

Technology Process of N-{[(Prop-2-en-1-yl)oxy]carbonyl}-L-phenylalanine

There total 13 articles about N-{[(Prop-2-en-1-yl)oxy]carbonyl}-L-phenylalanine 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%

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) + Allyl chloroformate (2937-50-0) → N-allyloxycarbonyl-(S)-phenylalanate (90508-20-6)

Guidance literature:

With sodium hydrogencarbonate; In 1,4-dioxane; water; at 20 ℃; for 19h;

DOI:10.1016/j.tetlet.2016.11.084

Reference yield: 96.0%

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) + diallyl dicarbonate (115491-93-5) → N-allyloxycarbonyl-(S)-phenylalanate (90508-20-6)

Guidance literature:

In 1,4-dioxane; water; for 18h; Heating;

DOI:10.1016/S0040-4039(01)81059-5

Reference yield: 92.0%

N-Alloc-phenylalanine (1-nosyl-5-nitroindol-3-yl)methyl ester → N-allyloxycarbonyl-(S)-phenylalanate (90508-20-6)

Guidance literature:

N-Alloc-phenylalanine (1-nosyl-5-nitroindol-3-yl)methyl ester; With 2-(N,N-dimethylamino)ethylthiol hydrochloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 20 ℃; for 0.25h; Inert atmosphere;

With hydrogenchloride; In diethyl ether; water; acetonitrile; Inert atmosphere;

DOI:10.1021/ol8008655

upstream raw materials:

L-phenylalanine

diallyl dicarbonate

Allyl chloroformate

N-(allyloxycarbonyloxy)succinimide

Downstream raw materials:

(S)-2-Allyloxycarbonylamino-3-phenyl-propionic acid (2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl ester

Alloc-Phe-Thr-OtBu

(S)-methyl-(N-allyloxycarbonyl)phenylalaninate

C₅₉H₆₉N₇O₁₄

Refernces

• 1、 Martin-Gómez, Helena,Albericio, Fernando,Tulla-Puche, Judit. "A Lasso-Inspired Bicyclic Peptide: Synthesis, Structure and Properties". supporting information. p. 19250 - 19257. Retrieved 2018/12/11.
• 2、 Ettari, Roberta,Pinto, Andrea,Previti, Santo,Tamborini, Lucia,Angelo, Ilenia C.,La Pietra, Valeria,Marinelli, Luciana,Novellino, Ettore,Schirmeister, Tanja,Zappalà, Maria,Grasso, Silvana,De Micheli, Carlo,Conti, Paola. "Development of novel dipeptide-like rhodesain inhibitors containing the 3-bromoisoxazoline warhead in a constrained conformation". . p. 7053 - 7060. Retrieved 2015/11/11.