threo-3-methyl-L-aspartic acid

Base Information

• Chemical Name: threo-3-methyl-L-aspartic acid
• CAS No.: 6061-13-8
• Molecular Formula: C5H9NO4
• Molecular Weight: 147.131
• UNII: X72YFG5KQE
• DSSTox Substance ID: DTXSID001031591
• Nikkaji Number: J750.143I
• Wikipedia: L-threo-3-Methylaspartate
• Wikidata: Q17037089
• Metabolomics Workbench ID: 52472
• ChEMBL ID: CHEMBL76739
• Mol file: 6061-13-8.mol

Synonyms:6061-13-8;threo-3-methyl-L-aspartic acid;(2S,3S)-2-Amino-3-methylsuccinic acid;(2S,3S)-2-amino-3-methylbutanedioic acid;L-threo-3-methylaspartate;X72YFG5KQE;L-Aspartic acid, 3-methyl-, (3S)-;L-Threo-3-methylaspartic acid;CHEBI:47980;(3S)-3-methyl-L-aspartic acid;(2s,3s)-3-Methyl-Aspartic Acid;3-Methyl-L-aspartic acid, (3S)-;2AS;2S,3S-3-METHYLASPARTIC ACID;threo-b-methylaspartate;UNII-X72YFG5KQE;(2s,3s)-3-methylaspartate;CHEMBL76739;SCHEMBL2895827;(2s,3s)-3-methylaspartic acid;Threo-beta-methyl-L-aspartic acid;DTXSID001031591;DB04538;(2S,3S)-2-Amino-3-methylsuccinicacid;THREO-.BETA.-METHYL-L-ASPARTIC ACID;C03618;Q17037089

Chemical Property of threo-3-methyl-L-aspartic acid

Chemical Property:

• XLogP3: -3.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 147.05315777
• Heavy Atom Count: 10
• Complexity: 156

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of threo-3-methyl-L-aspartic acid

There total 13 articles about threo-3-methyl-L-aspartic 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: 65.0%

C7H13NO4 → β-methylaspartic acid (642-92-2,1114-07-4,2955-50-2,4846-45-1,5941-19-5,6061-13-8,6667-60-3,7298-96-6,31571-69-4,86562-29-0,121570-10-3,127001-58-5)

Guidance literature:

With sodium hydroxide; In water; at 20 ℃; for 24h;

DOI:10.1021/jo701461t

Reference yield:

coprisamide C → D-Alanine (338-69-2,25191-17-7,18875-37-1) + L-valine (72-18-4,25609-85-2,7004-03-7,921-10-8) + (S)-2,3-diaminopropionic acid (515-94-6,1915-96-4,4033-39-0,6018-54-8) + D-Serine (312-84-5,83245-15-2) + (R)-leucine (328-38-1,21675-61-6,25248-98-0,70-45-1) + (2S,3S)-3-methylaspartic acid (6061-13-8)

Guidance literature:

With hydrogenchloride; In water; at 100 ℃; for 2h;

DOI:10.1021/acs.jnatprod.0c00864

Reference yield:

(3S,6R)-2,5-dimethoxy-3-((2'R)-methoxypropionyl)-6-isopropyl-3,6-dihydropyrazine → D-Val-OH (640-68-6,25609-85-2,7004-03-7,921-10-8) + (2S,3S)-3-methylaspartic acid (6061-13-8) + erythro-β-methyl-L-aspartate (7298-96-6)

Guidance literature:

With hydrogenchloride; sodium hydroxide; Yield given. Multistep reaction. Title compound not separated from byproducts; 1.) acetonitrile, RT, 12 h, 2.) acetonitrile, 70 deg C, 15 min;

DOI:10.1016/S0957-4166(00)80221-9

upstream raw materials:

Ethyl 2-bromopropionate

ethyl 2-acetamido-2-cyanoacetate

diethyl oxalpropionate

2-acetylaminomalonic acid diethyl ester

Downstream raw materials:

(R)-3-amino-2-methylpropanoic acid

(S)-(+)-β²-homoalanine

Mesaconic acid

(+/-)-threo-2-benzyloxycarbonylamino-3-methyl-succinic acid

Refernces

• 1、 Soengas, Raquel G.,Estévez, Amalia M.. "Indium-mediated allylation and Reformatsky reaction on glyoxylic oximes under ultrasound irradiation". experimental part. p. 916 - 920. Retrieved 2012/06/04.
• 2、 Archer, Catherine H.,Thomas, Neil R.,Gani, David. "Syntheses of (2S,3R)- and (2S,3R)2H>- 3-Methylaspartic acid: Slow Substrates for a syn-Elimination Reaction catalysed by Methylaspartase.". . p. 1141 - 1152. Retrieved 2007/10/02.