(S)-2-((tert-Butoxycarbonyl)amino)but-3-enoic acid

Base Information

• Chemical Name: (S)-2-((tert-Butoxycarbonyl)amino)but-3-enoic acid
• CAS No.: 91028-39-6
• Molecular Formula: C9H15NO4
• Molecular Weight: 201.222
• DSSTox Substance ID: DTXSID10449244
• Nikkaji Number: J786.071D
• Wikidata: Q82268655
• Mol file: 91028-39-6.mol

Synonyms:91028-39-6;(S)-2-((tert-Butoxycarbonyl)amino)but-3-enoic acid;Boc-L-Vinylglycine;(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]but-3-enoic acid;MFCD02682487;SCHEMBL6291038;Boc-L-vinylglycine, AldrichCPR;DTXSID10449244;3-Butenoic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-, (2S)-;BS-49942;N-(tert-Butoxycarbonyl)-2-vinyl-L-glycine;(S)-2-((tert-Butoxycarbonyl)amino)but-3-enoicacid;(2S)-2-{[(tert-butoxy)carbonyl]amino}but-3-enoic acid

Chemical Property of (S)-2-((tert-Butoxycarbonyl)amino)but-3-enoic acid

Chemical Property:

• Boiling Point: 342.7±35.0 °C(Predicted)
• Density: 1.120±0.06 g/cm3(Predicted)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 201.10010796
• Heavy Atom Count: 14
• Complexity: 242

Purity/Quality:

99% ^*data from raw suppliers

(S)-2-((tert-Butoxycarbonyl)amino)but-3-enoicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (S)-2-((tert-Butoxycarbonyl)amino)but-3-enoic acid

There total 13 articles about (S)-2-((tert-Butoxycarbonyl)amino)but-3-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: 87.0%

di-tert-butyl dicarbonate (24424-99-5) + (S)-2-aminobut-3-enoic acid hydrochloride (75266-38-5) → L-2-<<(tert-Butyloxy)carbonyl>amino>-3-butenoic Acid (91028-39-6)

Guidance literature:

With sodium hydrogencarbonate; In 1,4-dioxane; water; for 2h; Heating;

DOI:10.1021/jo01312a002

Reference yield: 80.0%

tert-butyl [(1S)-1-(hydroxymethyl)prop-2-en-1-yl]carbamate (91103-37-6) → L-2-<<(tert-Butyloxy)carbonyl>amino>-3-butenoic Acid (91028-39-6)

Guidance literature:

With jones reagent; In acetone; at 20 ℃; for 3h;

DOI:10.1021/ol049159x

Reference yield: 65.0%

(S)-2-amino-3-butenoic acid (70982-53-5) + di-tert-butyl dicarbonate (24424-99-5) → L-2-<<(tert-Butyloxy)carbonyl>amino>-3-butenoic Acid (91028-39-6)

Guidance literature:

With sodium hydroxide; In water; tert-butyl alcohol; Ambient temperature;

DOI:10.1021/jo961446u

upstream raw materials:

di-tert-butyl dicarbonate

(S)-2-aminobut-3-enoic acid hydrochloride

(S)-2-amino-3-butenoic acid

(3S,4S)-N-(tert-butoxycarbonyl)-4,5-O-isopropylidene-4,5-dihydroxypent-1-en-3-amine

Downstream raw materials:

L-2-<<(tert-Butyloxy)carbonyl>amino>butanoyl-d-α-phenylethylamide

(3S,6S,9S)-methyl 2-oxo-3--1-azabicyclo<4.3.0>nonane-9-carboxylate

methyl (S)-2-(tert-bytoxycarbonylamino)but-3-enoate

(4S)-vinylglycine trifluoroacetate

Refernces

• 1、 Dondoni, Alessandro,Giovannini, Pier Paolo,Perrone, Daniela. "Cross-metathesis of C-allyl iminosugars with alkenyl oxazolidines as a key step in the synthesis of C-iminoglycosyl α-amino acids. A route to iminosugar containing C-glycopeptides". . p. 5508 - 5518. Retrieved 2007/10/03.
• 2、 Chandrasekhar,Raza, Abbas,Takhi, Mohamed. "Synthesis of unusual amino acids: N-(tert-butoxycarbonyl)-L-vinyl glycine and N-(tert-butoxycarbonyl)-L-homophenylalanine". . p. 423 - 428. Retrieved 2007/10/03.