N-Acetylthreonine

Base Information

• Chemical Name: N-Acetylthreonine
• CAS No.: 17093-74-2
• Molecular Formula: C6H11NO4
• Molecular Weight: 161.158
• Hs Code.: 2924199090
• UNII: V0E98V3R9O
• DSSTox Substance ID: DTXSID80168975
• Nikkaji Number: J441.064E
• Wikidata: Q27104560
• Metabolomics Workbench ID: 71626
• Mol file: 17093-74-2.mol

Synonyms:ammonium N-acetyl-L-threoninate;methylammonium N-acetyl-L-threoninate;N-acetylthreonine

Chemical Property of N-Acetylthreonine

Chemical Property:

• Vapor Pressure: 1.01E-09mmHg at 25°C
• Refractive Index: 1.489
• Boiling Point: 443.349 °C at 760 mmHg
• Flash Point: 221.93 °C
• PSA: 86.63000
• Density: 1.275 g/cm³
• LogP: -0.65260
• Storage Temp.: Store at RT.
• Solubility.: Methanol (Slightly), Water (Slightly, Sonicated)
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 161.06880783
• Heavy Atom Count: 11
• Complexity: 168

Purity/Quality:

99%, ^*data from raw suppliers

Acetyl-L-threonine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of N-Acetylthreonine

There total 12 articles about N-Acetylthreonine 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: 66.0%

L-threonine (72-19-5,134357-96-3,7013-32-3,82822-12-6) + acetic anhydride (108-24-7) → (2S,3R)-2-acetamido-3-hydroxybutanoic acid (17093-74-2)

Guidance literature:

With acetic acid; at 40 ℃; for 15h;

DOI:10.1016/S0040-4020(97)00059-8

Reference yield:

perchloric acid (7601-90-3) + DL-threonine (80-68-2,134357-96-3,7013-32-3,82822-12-6) + acetic anhydride (108-24-7) + acetic acid (64-19-7,77671-22-8) → O-Acetyl-dl-threonin (17012-42-9,44976-20-7,66701-14-2,89531-77-1) + N-acetyl-DL-theanine (17093-74-2,55024-18-5,55024-24-3)

Guidance literature:

at 25 ℃; Geschwindigkeit;

Reference yield:

L-threonine (72-19-5,134357-96-3,7013-32-3,82822-12-6) → (2S,3R)-2-acetamido-3-hydroxybutanoic acid (17093-74-2)

Guidance literature:

With acetic anhydride; In acetic acid; at 50 ℃; for 2.5h; Temperature; Time;

DOI:10.1016/j.tet.2013.06.027

upstream raw materials:

tetrachloromethane

perchloric acid

DL-threonine

acetic anhydride

Downstream raw materials:

N-acetyl-threonine methyl ester

D-allo-threonine

L-threonine

(Z)-methyl 2-acetamido-3-methoxyacrylate

Refernces

• 1、 Kochetova,Kustova,Kuritsyn. "Reactivity of α-Amino Acids in the Reaction with Esters in Aqueous–1,4-Dioxane Media". . p. 80 - 85. Retrieved 2018/03/09.
• 2、 Kikuchi, Mari,Konno, Hiroyuki. "Improved synthesis of d-allothreonine derivatives from l-threonine". . p. 7098 - 7101. Retrieved 2013/07/26.