(2S,3S)-2-hydroxy-3-methylbutanedioic acid

Base Information

• Chemical Name: (2S,3S)-2-hydroxy-3-methylbutanedioic acid
• CAS No.: 13398-41-9
• Molecular Formula: C₅H₈O₅
• Molecular Weight: 148.116
• DSSTox Substance ID: DTXSID501268600
• Nikkaji Number: J1.436.825F
• Wikidata: Q27103705
• Metabolomics Workbench ID: 51723
• Mol file: 13398-41-9.mol

Synonyms:L-threo-3-methylmalic acid;L-threo-3-Methylmalate;(2S,3S)-2-hydroxy-3-methylbutanedioic acid;SCHEMBL4820682;CHEBI:28456;DTXSID501268600;AKOS006377888;C06029;Q27103705;13398-41-9

Chemical Property of (2S,3S)-2-hydroxy-3-methylbutanedioic acid

Chemical Property:

• XLogP3: -0.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 148.03717335
• Heavy Atom Count: 10
• Complexity: 152

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of (2S,3S)-2-hydroxy-3-methylbutanedioic acid

There total 12 articles about (2S,3S)-2-hydroxy-3-methylbutanedioic 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:

(S,S)-diisopropyl tartrate + diisopropyl (2R,3S)-2-methyl-3-hydroxybutanedioate (874646-33-0) → (2S, 3S)-threo-β-methylmalic acid (13398-41-9,5380-36-9,5380-37-0) + (2S,3R)-3-methylmalic acid (85026-06-8,5380-36-9,5380-37-0)

Guidance literature:

(S,S)-diisopropyl tartrate; diisopropyl (2R,3S)-2-methyl-3-hydroxybutanedioate; With potassium hydroxide; water; In tetrahydrofuran; at 0 - 20 ℃; for 48h;

With hydrogenchloride; In water;

Reference yield:

(2S,3S)-3-methylaspartic acid (6061-13-8) → (2S, 3S)-threo-β-methylmalic acid (13398-41-9,5380-36-9,5380-37-0)

Guidance literature:

With cis-nitrous acid;

DOI:10.1016/S0040-4039(01)90254-0

Reference yield:

D,L-threo-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) → (2S, 3S)-threo-β-methylmalic acid (13398-41-9,5380-36-9,5380-37-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) acetone, MeOH, water; 2.) water, HCl, pH=3, EtOH

2: NaNO₂ / H₂O; H₂SO₄ / 0 - 25 °C

With sodium nitrite; In sulfuric acid; water;

DOI:10.1016/0040-4020(82)80081-1

upstream raw materials:

(2S,3S)-3-methylaspartic acid

D,L-threo-β-methylaspartic acid

diisopropyl (2R,3S)-2-methyl-3-hydroxybutanedioate

(E)-(2S,3S)-3-Hydroxy-2-methyl-hex-4-enoic acid

Downstream raw materials:

(2S,3S)-2-Hydroxy-3-methyl-bernsteinsaeuredimethylester

2-Methyl-3-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-succinic acid dimethyl ester

(2R,3R)-2-Methyl-3-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-succinic acid dimethyl ester

(2S,3R)-2-Methyl-3-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-succinic acid dimethyl ester