D-Asparagine methyl ester

Base Information

• Chemical Name: D-Asparagine methyl ester
• CAS No.: 108258-31-7
• Molecular Formula: C₅H₁₀N₂O₃
• Molecular Weight: 146.146
• Hs Code.: 2924199090
• DSSTox Substance ID: DTXSID20373425
• Wikidata: Q72443883
• Mol file: 108258-31-7.mol

Synonyms:D-Asparagine methyl ester;108258-31-7;methyl (2R)-2,4-diamino-4-oxobutanoate;D-Asparaginemethylester;D-Asparaginemethyl ester;D-asparagine,methyl ester;SCHEMBL6250353;DTXSID20373425;EN300-7039312;METHYL (2R)-2-AMINO-3-CARBAMOYLPROPANOATE;Q-103180

Chemical Property of D-Asparagine methyl ester

Chemical Property:

• Vapor Pressure: 0.000189mmHg at 25°C
• Boiling Point: 328.5oC at 760 mmHg
• PKA: 16.01±0.40(Predicted)
• Flash Point: 198.1oC
• PSA: 96.40000
• Density: 1.223g/cm3
• LogP: 0.21210
• Storage Temp.: 2-8°C
• XLogP3: -1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 146.06914219
• Heavy Atom Count: 10
• Complexity: 146

Purity/Quality:

98%min ^*data from raw suppliers

D-AsparagineMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(CC(=O)N)N
• Isomeric SMILES: COC(=O)[C@@H](CC(=O)N)N
• Uses: D-Asparagine Methyl Ester is a protected form of D-Asparagine (A788960) which is an isomer of L-Asparagine (A790005). L-Asparagine is used by bacteria (such as Saccharomyces cerevisiae) as a sole nitrogen source for replication. L-Asparagine is also a competitive inhibitor of staphylococcal L-asparaginase and is used as a reagent to synthesize peptide antibiotics.

Technology Process of D-Asparagine methyl ester

There total 3 articles about D-Asparagine methyl ester 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: 78.0%

methanol (67-56-1) + N-tert-butyloxycarbonylasparagine (7536-55-2) → methyl (S)-2,4-diamino-4-oxobutanoate (6384-09-4,108258-31-7,119991-47-8)

Guidance literature:

With ammonium cerium(IV) nitrate; Heating;

DOI:10.1016/j.tetlet.2004.01.136

Reference yield: 76.0%

N-(benzyloxycarbonyl)asparagine methyl ester (4668-37-5) → methyl (S)-2,4-diamino-4-oxobutanoate (6384-09-4,108258-31-7,119991-47-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 4h;

Reference yield:

Nα-(tert-butoxycarbonyl)-(S)-asparagine methyl ester (124842-28-0) → methyl (S)-2,4-diamino-4-oxobutanoate (6384-09-4,108258-31-7,119991-47-8)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃;

upstream raw materials:

N-(benzyloxycarbonyl)asparagine methyl ester

methanol

N-tert-butyloxycarbonylasparagine

N^α-(tert-butoxycarbonyl)-(S)-asparagine methyl ester

Downstream raw materials:

(6S,9S,15S)-methyl 15-(2-amino-2-oxoethyl)-6,9-dibenzyl-2,2-dimethyl-4,7,10,13-tetraoxo-3-oxa-5,8,11,14-tetraazahexadecan-16-oate

Refernces

• 1、 -. "ETHER COMPOUNDS AND USES THEREOF". Paragraph 0235. . Retrieved 2019/03/12.
• 2、 Howes, Colin,Alcock, Nathaniel W.,Golding, Bernard T.,McCabe, Richard W.. "Cyclo-(L-asparagyl-L-asparagyl) : Preparation and Crystal Structure". . p. 2287 - 2291. Retrieved 2007/10/02.