(4S,5R)-5-methyl-2-oxo-1,3-oxazolidine-4-carboxylic acid

Base Information

• Chemical Name: (4S,5R)-5-methyl-2-oxo-1,3-oxazolidine-4-carboxylic acid
• CAS No.: 1195-20-6
• Molecular Formula: C₅H₇NO₄
• Molecular Weight: 145.115
• European Community (EC) Number: 873-774-8
• DSSTox Substance ID: DTXSID401225104
• Nikkaji Number: J618.590H
• Wikidata: Q27464216
• Mol file: 1195-20-6.mol

Synonyms:1195-20-6;(4S,5R)-5-methyl-2-oxooxazolidine-4-carboxylic acid;(4S,5R)-5-methyl-2-oxo-1,3-oxazolidine-4-carboxylic acid;SCHEMBL691410;KYNKAUUXUQOZSQ-GBXIJSLDSA-N;DTXSID401225104;AKOS026729905;EN300-126390;(4S,5R)-5-methyl-2-oxooxazolidine-4-carboxylicacid;Q27464216

Chemical Property of (4S,5R)-5-methyl-2-oxo-1,3-oxazolidine-4-carboxylic acid

Chemical Property:

• XLogP3: -0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 145.03750770
• Heavy Atom Count: 10
• Complexity: 179

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1C(NC(=O)O1)C(=O)O
• Isomeric SMILES: C[C@@H]1[C@H](NC(=O)O1)C(=O)O

Technology Process of (4S,5R)-5-methyl-2-oxo-1,3-oxazolidine-4-carboxylic acid

There total 18 articles about (4S,5R)-5-methyl-2-oxo-1,3-oxazolidine-4-carboxylic 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: 64.0%

(2R,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutanoic acid (119221-16-8) → (4R,5R)-5-methyl-2-oxooxazolidine-4-carboxylic acid (1195-19-3,1195-20-6,37791-36-9,50896-26-9,98302-45-5,122871-70-9)

Guidance literature:

With sodium hydroxide; In methanol; water; for 3.75h; Cooling with ice;

DOI:10.1002/psc.3228

Reference yield:

N6-(L-threonylcarbamoyl)adenosine-5'-monophosphate (42583-85-7) → L-threonine (72-19-5,134357-96-3,7013-32-3,82822-12-6) + L-threonine isocyanate + (5R,4S)-5-methyl-2-oxazolidinone-4-carboxylic acid (1195-20-6) + L-threonine N-carboxyanhydride (33043-58-2) + 5'-adenosine monophosphate (61-19-8,24937-83-5,67583-85-1)

Guidance literature:

In aq. phosphate buffer; water-d2; at 25 ℃; for 44h; pH=6;

DOI:10.1021/bi301233d

Reference yield:

bis(trichloromethyl) carbonate (32315-10-9) + (O-tert-butyl)-L-threonine (4378-13-6,201353-89-1) → (5R,4S)-5-methyl-2-oxazolidinone-4-carboxylic acid (1195-20-6) + L-threonine N-carboxyanhydride (33043-58-2)

Guidance literature:

bis(trichloromethyl) carbonate; (O-tert-butyl)-L-threonine; In tetrahydrofuran; for 3h; Reflux;

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/bi301233d

upstream raw materials:

N-benzyloxycarbonyl-DL-threonine

DL-threonine

benzyl chloroformate

3-benzoyl-5t-methyl-2-oxo-oxazolidine-4r-carboxylic acid methyl ester

Downstream raw materials:

L-threonine

methyl (4S,5R)-5-methyl-2-carbonyloxazolidine-4-carboxylate

(4R,5R)-5-methyl-4-(2-oxo-2-phenylethyl)oxazolidin-2-one

benzyl (4S,5R)-5-methyl-2-oxo-1,3-oxazolidine-4-carboxylate