O-Methyl-L-threonine

Base Information

• Chemical Name: O-Methyl-L-threonine
• CAS No.: 4144-02-9
• Molecular Formula: C5H11NO3
• Molecular Weight: 133.147
• Hs Code.: 2922500090
• European Community (EC) Number: 690-841-5
• UNII: OAI4PJX6XS
• DSSTox Substance ID: DTXSID20195962,DTXSID701031342
• Nikkaji Number: J669.036J
• Wikidata: Q27285544
• ChEMBL ID: CHEMBL1234983
• Mol file: 4144-02-9.mol

Synonyms:O-methyl threonine;O-methyl threonine, (L-Thr)-isomer

Chemical Property of O-Methyl-L-threonine

Chemical Property:

• Vapor Pressure: 0.008mmHg at 25°C
• Melting Point: 214-216 °C
• Refractive Index: 1.461
• Boiling Point: 248 °C at 760 mmHg
• PKA: 2.12±0.10(Predicted)
• Flash Point: 103.8 °C
• PSA: 72.55000
• Density: 1.143 g/cm³
• LogP: 0.13350
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly, Sonicated), Methanol (Slightly), Water (Sparingly)
• XLogP3: -3.1
• 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:

98%,99%, ^*data from raw suppliers

O-Methyl-L-threonine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

Useful:

• Canonical SMILES: CC(C(C(=O)O)N)OC
• Isomeric SMILES: C[C@H]([C@@H](C(=O)O)N)OC
• Uses: O-Methyl-L-threonine can be used as photoresists.

Technology Process of O-Methyl-L-threonine

There total 18 articles about O-Methyl-L-threonine 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: 90.0%

N-Trt-Thr (85918-01-0,115201-03-1) → O-methyl-L-threonine (2076-53-1,2076-57-5,4144-02-9,4385-90-4,34223-42-2,88642-93-7,104195-79-1,104195-80-4)

Guidance literature:

With acetic acid; In ethanol; for 24h; Ambient temperature;

DOI:10.1016/S0040-4020(01)88549-5

Reference yield:

methyl (2S,3R)-2-{[(benzyloxy)carbonyl]amino}-3-methoxybutanoate (4144-14-3) → O-methyl-L-threonine (4144-02-9)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. LiOH / tetrahydrofuran

2: H₂ / Pd/BaSO₄

With lithium hydroxide; hydrogen; Pd-BaSO₄; In tetrahydrofuran;

DOI:10.1016/j.bmcl.2004.12.082

Reference yield:

N-Boc-L-Thr(Me)-OMe → O-methyl-L-threonine (4144-02-9)

Guidance literature:

With hydrogenchloride; at 120 ℃; for 16h;

DOI:10.1021/jo800583b

upstream raw materials:

N-formyl-O-methyl-L_s-threonine

Benzyloxycarbonyl-O-methyl-threonin

methyl (2S,3R)-2-{[(benzyloxy)carbonyl]amino}-3-methoxybutanoate

O-methyl-DL-threonine

Downstream raw materials:

N-formyl-O-methyl-DL-allothreonine

N-formyl-O-methyl-DL-threonine

L-threonine

DL-threonine

Refernces

• 1、 Kang, Hahk-Soo,Sturdy, Megan,Krunic, Aleksej,Kim, Hyunjung,Shen, Qi,Swanson, Steven M.,Orjala, Jimmy. "Minutissamides E-L, antiproliferative cyclic lipodecapeptides from the cultured freshwater cyanobacterium cf. Anabaena sp.". supporting information. p. 6134 - 6143. Retrieved 2012/11/07.
• 2、 Zampella, Angela,Sepe, Valentina,Luciano, Paolo,Bellotta, Filomena,Monti, Maria Chiara,D'Auria, Maria Valeria,Jepsen, Trine,Petek, Sylvain,Adeline, Marie-Therese,Laprevote, Olivier,Aubertin, Anne-Marie,Debitus, Cecile,Poupat, Christiane,Ahond, Alain. "Homophymine A, an anti-HIV cyclodepsipeptide from the sponge Homophymia sp.". . p. 5319 - 5327. Retrieved 2008/12/22.