D-Serine, N-acetyl-, methyl ester (9CI)

Base Information

• Chemical Name: D-Serine, N-acetyl-, methyl ester (9CI)
• CAS No.: 288402-26-6
• Molecular Formula: C₆H₁₁NO₄
• Molecular Weight: 161.158
• Mol file: 288402-26-6.mol

Synonyms:Serine,N-acetyl-, methyl ester, DL- (7CI); N-acetyl-D-serine methyl ester

Chemical Property of D-Serine, N-acetyl-, methyl ester (9CI)

Chemical Property:

• PSA: 75.63000
• LogP: -0.95270

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of D-Serine, N-acetyl-, methyl ester (9CI)

There total 15 articles about D-Serine, N-acetyl-, methyl ester (9CI) 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: 94.0%

R-(-)-serine methyl ester hydrochloride (5874-57-7) + acetyl chloride (75-36-5) → (R)-methyl 2-acetamido-3-hydroxypropionate (288402-26-6)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.1021/jm901563p

Reference yield: 93.0%

methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride (5680-80-8) + acetic acid (64-19-7,77671-22-8) → (S)-methyl 2-acetamido-3-hydroxypropanoate (2311-26-4,54322-41-7,55299-56-4,288402-26-6)

Guidance literature:

With triethylamine; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1021/jo00049a019

Reference yield: 84.0%

methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride (5680-80-8) + acetyl chloride (75-36-5) → (S)-methyl 2-acetamido-3-hydroxypropanoate (2311-26-4,54322-41-7,55299-56-4,288402-26-6)

Guidance literature:

With triethylamine; In dichloromethane; at -5 - 20 ℃; for 2h;

DOI:10.1016/j.tet.2008.07.015

upstream raw materials:

N-Acetyl-3-O-p-tolylsulfonyl-DL-serin-methylester

diazomethane

2-aminomalonic acid

acetic anhydride

Refernces

• 1、 Sayama, Misa,Uwamizu, Akiharu,Ikubo, Masaya,Chen, Luying,Yan, Ge,Otani, Yuko,Inoue, Asuka,Aoki, Junken,Ohwada, Tomohiko. "Switching Lysophosphatidylserine G Protein-Coupled Receptor Agonists to Antagonists by Acylation of the Hydrophilic Serine Amine". . p. 10059 - 10101. Retrieved 2021/07/28.
• 2、 Nathanael, Joses G.,Wille, Uta. "Oxidative Damage in Aliphatic Amino Acids and Di- and Tripeptides by the Environmental Free Radical Oxidant NO3?: the Role of the Amide Bond Revealed by Kinetic and Computational Studies". . p. 3405 - 3418. Retrieved 2019/03/11.