(S)-2-(((Benzyloxy)carbonyl)amino)pent-4-enoic acid

Base Information

• Chemical Name: (S)-2-(((Benzyloxy)carbonyl)amino)pent-4-enoic acid
• CAS No.: 78553-51-2
• Molecular Formula: C13H15NO4
• Molecular Weight: 249.266
• DSSTox Substance ID: DTXSID90472393
• Nikkaji Number: J500.176E
• Wikidata: Q82301308
• Mol file: 78553-51-2.mol

Synonyms:78553-51-2;(S)-2-(((Benzyloxy)carbonyl)amino)pent-4-enoic acid;(S)-2-(benzyloxycarbonylamino)pent-4-enoic acid;(2S)-2-(phenylmethoxycarbonylamino)pent-4-enoic acid;(2S)-2-{[(benzyloxy)carbonyl]amino}pent-4-enoic acid;(S)-N-CBZ-2-(AMINO)PENT-4-ENOIC ACID;(2S)-2-(((Benzyloxy)carbonyl)amino)pent-4-enoic acid;CBZ-ALPHA-ALLYL-L-GLY;Z-Algly-OH;4-Pentenoic acid, 2-[[(phenylmethoxy)carbonyl]amino]-, (2S)-;SCHEMBL1162401;DTXSID90472393;DGEZDWGCGXHLEW-NSHDSACASA-N;MFCD02094548;AKOS005264715;CS-W021156;DS-4454;HY-W040416;PD197110;Cbz-|A inverted exclamation mark-allyl-L-Gly;EN300-6977581;A865018;(S)-2-(((Benzyloxy)carbonyl)amino)pent-4-enoicacid;(2S)-2-{[(Benzyloxy)carbonyl]amino}-4-pentenoic acid;(2S)-2-[[(phenylmethoxy)carbonyl]amino]-4-Pentenoic acid

Chemical Property of (S)-2-(((Benzyloxy)carbonyl)amino)pent-4-enoic acid

Chemical Property:

• PSA: 75.63000
• LogP: 2.33300
• Storage Temp.: 2-8°C
• XLogP3: 2.2
• 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

(2S)-2-[[(phenylmethoxy)carbonyl]amino]-4-Pentenoicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CCC(C(=O)O)NC(=O)OCC1=CC=CC=C1
• Isomeric SMILES: C=CC[C@@H](C(=O)O)NC(=O)OCC1=CC=CC=C1
• Uses: (2S)-2-[[(phenylmethoxy)carbonyl]amino]-4-Pentenoic acid is a useful building block, and has been used in the regioselective preparation of nonracemic silylated amino acids.

Technology Process of (S)-2-(((Benzyloxy)carbonyl)amino)pent-4-enoic acid

There total 11 articles about (S)-2-(((Benzyloxy)carbonyl)amino)pent-4-enoic acid 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%

N-(Benzyloxycarbonyloxy)succinimide (13139-17-8) + L-allylglycine (16338-48-0) → (S)-2-(benzyloxycarbonylamino)pent-4-enoic acid (78553-51-2)

Guidance literature:

With water; triethylamine; In 1,4-dioxane;

Reference yield: 98.0%

L-allylglycine (16338-48-0) + benzyl chloroformate (501-53-1,94274-21-2) → (S)-2-(benzyloxycarbonylamino)pent-4-enoic acid (78553-51-2)

Guidance literature:

With sodium hydrogencarbonate; In water; at 20 ℃; for 5h;

DOI:10.1002/ejoc.200800066

Reference yield: 24.0%

N-Acetyl-α-allylglycine (50299-14-4) + benzyl chloroformate (501-53-1,94274-21-2) → N-Acetyl-D-α-allylglycine (121786-40-1) + (S)-2-(benzyloxycarbonylamino)pent-4-enoic acid (78553-51-2) + (2S)-2-N-acetylaminopent-4-enoic acid (149117-86-2)

Guidance literature:

N-Acetyl-α-allylglycine; With thermococcus litoralis L-aminoacylase; tris hydrochloride; at 70 ℃; pH=8; Resolution of racemate; Large scale; Enzymatic reaction;

benzyl chloroformate; With sodium hydroxide; In tetrahydrofuran; water; at 5 - 10 ℃; pH=7.5 - 8.5; Large scale;

DOI:10.1021/op020017x

upstream raw materials:

L-allylglycine

benzyl chloroformate

((S)-2-Oxo-oxetan-3-yl)-carbamic acid benzyl ester

vinylmagnesium chloride

Downstream raw materials:

(R)-2-tert-Butoxycarbonylamino-pent-4-enoic acid 2-((S)-2-benzyloxycarbonylamino-pent-4-enoyloxy)-ethyl ester

(S)-methyl 2-((S)-2-(benzyloxycarbonylamino)pent-4-enamido)-5-(1,3-dioxolan-2-yl)pentanoate

methyl (2S)-2-[N-(benzyloxycarbonyl)amino]pent-4-enoate

tert-butyl (S)-2-(benzyloxycarbonylamino)pent-4-enoate

Refernces

• 1、 Angelini, Lucrezia,Govaerts, Sebastian,Hampton, Charlotte,Leonori, Daniele,Malet-Sanz, Laia,Ruffoni, Alessandro. "Photoinduced Olefin Diamination with Alkylamines". supporting information. p. 15021 - 15028. Retrieved 2020/06/17.
• 2、 -. "Conformation-constrained entirely-synthetic macrocyclic compounds". Paragraph 0782; 1408. . Retrieved 2016/10/07.