(2S,3R)-methyl 2-amino-3-hydroxybutanoate

Base Information

• Chemical Name: (2S,3R)-methyl 2-amino-3-hydroxybutanoate
• CAS No.: 3373-59-9
• Molecular Formula: C5H11NO3
• Molecular Weight: 133.147
• Hs Code.: 2922509090
• European Community (EC) Number: 222-158-1
• UNII: 9FOK073U22
• DSSTox Substance ID: DTXSID50955339
• Nikkaji Number: J205.460D
• ChEMBL ID: CHEMBL1229068
• Mol file: 3373-59-9.mol

Synonyms:3373-59-9;(2S,3R)-methyl 2-amino-3-hydroxybutanoate;L-THREONINE METHYL ESTER;H-Thr-OMe;Methyl threoninate;Methyl L-threoninate;threonine methyl ester;L-Threoninemethyl ester;UNII-9FOK073U22;methyl (2S,3R)-2-amino-3-hydroxybutanoate;9FOK073U22;EINECS 222-158-1;EC 222-158-1;Threonine, methyl ester;NSC-287508;L-Threonine methyl;L-Threonine Methylester;SCHEMBL155155;CHEMBL1229068;DTXSID50955339;TVHCXXXXQNWQLP-DMTCNVIQSA-N;THREONINE, METHYL ESTER, L-;AKOS006238777;NSC 287508;METHYL 2(S):3(R)-THREONINATE;(2S,3R)-methyl2-amino-3-hydroxybutanoate;methyl (2S,3R)-2-amino-3-hydroxybutyrate;D87823;EN300-371776;Q27272500

Chemical Property of (2S,3R)-methyl 2-amino-3-hydroxybutanoate

Chemical Property:

• Vapor Pressure: 0.00744mmHg at 25°C
• Melting Point: 213-214 °C
• Refractive Index: 1.461
• Boiling Point: 238.58 °C at 760 mmHg
• PKA: 12.02±0.45(Predicted)
• Flash Point: 98.09 °C
• PSA: 72.55000
• Density: 1.143 g/cm³
• LogP: -0.43220
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• XLogP3: -1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 133.07389321
• Heavy Atom Count: 9
• Complexity: 104

Purity/Quality:

99.9% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (2S,3R)-methyl 2-amino-3-hydroxybutanoate

There total 16 articles about (2S,3R)-methyl 2-amino-3-hydroxybutanoate 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: 92.0%

methanol (67-56-1) + DL-threonine (72-19-5,80-68-2,144-98-9,632-20-2,2676-21-3,7004-04-8,24830-94-2,28954-12-3,36676-50-3,134357-96-3,7013-32-3,82822-12-6) → Z-threonine methyl ester (3373-59-9,53216-06-1,68331-48-6,79617-28-0,82679-55-8,118525-51-2)

Guidance literature:

With thionyl chloride; at 0 - 20 ℃;

DOI:10.1016/j.bmcl.2006.12.050

Reference yield: 80.0%

methanol (67-56-1) + L-threonine (72-19-5,134357-96-3,7013-32-3,82822-12-6) → L-threonine methyl ester (3373-59-9)

Guidance literature:

With thionyl chloride; at 0 ℃; for 25h; Temperature; Reflux;

Reference yield: 70.0%

N-(tert-butoxycarbonyl)-l-threonine methyl ester (60538-19-4,79479-07-5,96099-84-2,113525-91-0) → L-threonine methyl ester (3373-59-9)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; at 10 - 25 ℃; for 2h;

upstream raw materials:

methanol

(2S,3S)-2-amino-3-hydroxybutanoic acid

DL-threonine

rac-allo-threonine

Downstream raw materials:

Z(OMe)-Cys(Ad)-Val-Thr-OMe

Z(OMe)-Phe-Val-Pro-Thr-OMe

Z(OMe)-Cys(Ad)-Val-Thr-OMe

C₆H₉NO₃

Refernces

Facile preparation of oxazole-4-carboxylates and 4-ketones from aldehydes using 3-oxazoline-4-carboxylates as intermediates

10.1021/ol1012789

The research focuses on the development of a novel two-step synthesis method for oxazole-4-carboxylates from aldehydes, utilizing 3-oxazoline-4-carboxylates as synthetic intermediates. The main content involves a one-pot condensation-oxidation of aldehydes with serine or threonine methyl ester to form 3-oxazoline-4-carboxylates, followed by oxidation to obtain the desired oxazole-4-carboxylates. The experiments employed various reactants, including aldehydes, serine or threonine methyl ester, DABCO, NCS, and different oxidizing agents such as NBS, K2CO3, and molecular sieves. The analyses used to monitor the reactions and characterize the products included thin-layer chromatography (TLC), and the synthesized compounds were confirmed through detailed spectroscopic data provided in the supporting information. This method offers a more efficient and straightforward approach to synthesize oxazole derivatives compared to the traditional three-step procedures, and it also explores the reactivity of 3-oxazoline-4-carboxylates with Grignard reagents, leading to the facile preparation of 4-keto-oxazole derivatives.

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