Methyl D-serinate

Base Information

• Chemical Name: Methyl D-serinate
• CAS No.: 24184-43-8
• Molecular Formula: C₄H₉NO₃
• Molecular Weight: 119.12
• European Community (EC) Number: 246-067-1
• DSSTox Substance ID: DTXSID50178889
• Nikkaji Number: J237.939B
• Wikidata: Q83049390
• Mol file: 24184-43-8.mol

Synonyms:Methyl D-serinate;24184-43-8;D-Serine, methyl ester;D-serine methyl ester;(R)-Methyl 2-amino-3-hydroxypropanoate;methyl (2R)-2-amino-3-hydroxypropanoate;EINECS 246-067-1;d-serine methyl;D-Ser-OMe;(D)-serine methyl ester;SCHEMBL47274;DTXSID50178889;AKOS006341295;(R)-Methyl2-amino-3-hydroxypropanoate;methyl (R)-2-amino-3-hydroxypropanoate;CS-0069633;EN300-178157;A912953;(R)-2-amino-3-hydroxy-propionic acid methyl ester;F8884-9964

Chemical Property of Methyl D-serinate

Chemical Property:

• Vapor Pressure: 0.00953mmHg at 25°C
• Boiling Point: 234.7°Cat760mmHg
• PKA: 11.95±0.10(Predicted)
• Flash Point: 95.8°C
• PSA: 72.55000
• Density: 1.195g/cm³
• LogP: -0.82070
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 119.058243149
• Heavy Atom Count: 8
• Complexity: 83.4

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(CO)N
• Isomeric SMILES: COC(=O)[C@@H](CO)N

Technology Process of Methyl D-serinate

There total 14 articles about Methyl D-serinate 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: 100.0%

methanol (67-56-1) + D-Serine (312-84-5,83245-15-2) → D-serine methyl ester (2104-89-4,2788-84-3,24184-43-8)

Guidance literature:

With hydrogenchloride; for 18h; Heating;

DOI:10.1016/S0040-4039(00)74203-1

Reference yield: 96.0%

methanol (67-56-1) + serin (302-84-1,83245-15-2) → Ser-OMe (2104-89-4,2788-84-3,24184-43-8)

Guidance literature:

With thionyl chloride; at 0 - 20 ℃;

DOI:10.1016/j.bmcl.2006.12.050

Reference yield: 90.0%

R-(-)-serine methyl ester hydrochloride (5874-57-7) → D-serine methyl ester (2104-89-4,2788-84-3,24184-43-8)

Guidance literature:

With triethylamine; In acetonitrile; at 20 ℃; for 1h;

DOI:10.1016/j.bmc.2008.08.055

upstream raw materials:

methanol

serin

L-serin

N-tert-butoxycarbonylserine methyl ester

Downstream raw materials:

N-[N-(toluene-4-sulfonyl)-glycyl]-serine methyl ester

2-(3,5-dioxo-1,2-diphenyl-pyrazolidin-4-ylidene)-oxazolidine-4-carboxylic acid methyl ester

2-((E)-2-Benzyloxycarbonylamino-but-2-enoylamino)-3-hydroxy-propionic acid methyl ester

2-((E)-2-Benzyloxycarbonylamino-3-phenyl-acryloylamino)-3-hydroxy-propionic acid methyl ester

Refernces

• 1、 Dong, Mengxian,Wang, Jie,Wu, Shijie,Zhao, Yang,Ma, Yangyang,Xing, Yongfei,Cao, Fei,Li, Longfei,Li, Zhenqiu,Zhu, Huajie. "Catalytic Mechanism Study on the 1,2- and 1,4-Transfer Hydrogenation of Ketimines and β-Enamino Esters Catalyzed by Axially Chiral Biscarboline-Based Alcohols". supporting information. p. 4602 - 4610. Retrieved 2019/08/30.
• 2、 Takahashi, Kazunori,Ito, Takumi,Yamada, Wataru,Tsubuki, Masayoshi,Honda, Toshio. "A formal synthesis of (–)-kainic acid by means of SMI2-mediated radical cyclization". . p. 882 - 894. Retrieved 2018/06/04.