(S)-Methyl 2-(((benzyloxy)carbonyl)amino)but-3-enoate

Base Information

• Chemical Name: (S)-Methyl 2-(((benzyloxy)carbonyl)amino)but-3-enoate
• CAS No.: 75266-40-9
• Molecular Formula: C13H15NO4
• Molecular Weight: 249.266
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID10448494
• Nikkaji Number: J1.692.576D
• Wikidata: Q72441888
• Mol file: 75266-40-9.mol

Synonyms:75266-40-9;(S)-Methyl 2-(((benzyloxy)carbonyl)amino)but-3-enoate;Z-L-ALPHA-VINYL-GLY-OME;(S)-2-(BENZYLOXYCARBONYLAMINO)-3-BUTENOIC ACID METHYL ESTER;Z-L-a-vinyl-Gly-OMe;(S)-Methyl 2-(benzyloxycarbonylamino)but-3-enoate;methyl (2S)-2-(phenylmethoxycarbonylamino)but-3-enoate;MFCD00145552;SCHEMBL930559;(S)-Methyl2-(((benzyloxy)carbonyl)amino)but-3-enoate;DTXSID10448494;YDGRSOXTMWVLOJ-NSHDSACASA-N;AMY21387;AKOS016009947;CS-W006316;DS-6106;A9596;C76405;methyl (S)-2-(((benzyloxy)carbonyl)amino)but-3-enoate;(S)-2-Benzyloxycarbonylamino-but-3-enoic acid methyl ester;(S)-Methyl 2-(((benZyloxy)carbonyl)amino)but-3-enoate (CbZ-L-Gly(Vinyl)-OMe)

Chemical Property of (S)-Methyl 2-(((benzyloxy)carbonyl)amino)but-3-enoate

Chemical Property:

• Melting Point: 35-36℃
• Boiling Point: 387.9±42.0 °C(Predicted)
• PKA: 10.49±0.46(Predicted)
• PSA: 64.63000
• Density: 1.153
• LogP: 2.03130
• Storage Temp.: 2-8°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 249.10010796
• Heavy Atom Count: 18
• Complexity: 297

Purity/Quality:

97% ^*data from raw suppliers

(S)-Methyl2-(((benzyloxy)carbonyl)amino)but-3-enoate 96% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(C=C)NC(=O)OCC1=CC=CC=C1
• Isomeric SMILES: COC(=O)[C@H](C=C)NC(=O)OCC1=CC=CC=C1

Technology Process of (S)-Methyl 2-(((benzyloxy)carbonyl)amino)but-3-enoate

There total 49 articles about (S)-Methyl 2-(((benzyloxy)carbonyl)amino)but-3-enoate 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: 94.0%

C19H19N3O8Se → N-benzyloxycarbonyl-L-α-vinylglycine methyl ester (75266-40-9)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; water; at 20 ℃; for 23h; chemoselective reaction; Inert atmosphere;

DOI:10.1002/ejoc.202001208

Reference yield: 83.0%

(2S)-2-benzyloxycarbonylamino-4-phenylselenyl-butyric acid methyl ester (104523-60-6) → N-benzyloxycarbonyl-L-α-vinylglycine methyl ester (75266-40-9)

Guidance literature:

With pyridine; dihydrogen peroxide; In dichloromethane; for 2h; Heating;

DOI:10.1021/jo0507439

Reference yield: 67.0%

benzyl (S)-1-(methoxycarbonyl)-3-(4-chlorophenylsulfinyl)propylcarbamate (1187361-43-8) → benzyl (S)-1-(methoxycarbonyl)-3-(4-chlorophenylthio)propylcarbamate (1187361-36-9) + (Z)-2-Benzyloxycarbonylamino-but-2-enoic acid methyl ester (60027-55-6,60027-61-4,70396-37-1) + N-benzyloxycarbonyl-L-α-vinylglycine methyl ester (75266-40-9)

Guidance literature:

at 190 ℃; for 0.25h; under 760 Torr;

DOI:10.1016/j.tetlet.2009.06.082

upstream raw materials:

Z-L-GluOMe

methyl (S)-2-<<(benzyloxy)carbonyl>amino>-4-(methylsulfinyl)butanoate

(2S)-2-benzyloxycarbonylamino-4-phenylselenyl-butyric acid methyl ester

(L)-methyl 2-benzyloxycarbonylamino-4-(2'-pyridylseleno)butanoate

Downstream raw materials:

(R)-2-Benzyloxycarbonylamino-3-chloro-4-phenylselanyl-butyric acid methyl ester

methyl (2S)-2-(N-benzyloxycarbonyl)amino-4-butanoate

(S)-((R)-3-Benzenesulfonyl-4,5-dihydro-isoxazol-5-yl)-benzyloxycarbonylamino-acetic acid methyl ester

(S)-((S)-3-Benzenesulfonyl-4,5-dihydro-isoxazol-5-yl)-benzyloxycarbonylamino-acetic acid methyl ester