benzyl (2R)-2-aminopropanoate

Base Information

• Chemical Name: benzyl (2R)-2-aminopropanoate
• CAS No.: 17831-02-6
• Molecular Formula: C10H13NO2
• Molecular Weight: 179.219
• DSSTox Substance ID: DTXSID301307630
• Nikkaji Number: J260.470A
• Mol file: 17831-02-6.mol

Synonyms:D-alanine benzyl ester;benzyl (2R)-2-aminopropanoate;17831-02-6;D-Alanine, phenylmethyl ester;benzyl D-alaninate;D-alanine, benzyl ester;D-Alanine phenylmethyl ester;benzyl(2R)-2-aminopropanoate;SCHEMBL2135198;DTXSID301307630;D-Alanine benzyl ester, AldrichCPR;AKOS017427025;CCG-256310;D86017;EN300-106957

Chemical Property of benzyl (2R)-2-aminopropanoate

Chemical Property:

• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 179.094628657
• Heavy Atom Count: 13
• Complexity: 164

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(=O)OCC1=CC=CC=C1)N
• Isomeric SMILES: C[C@H](C(=O)OCC1=CC=CC=C1)N

Technology Process of benzyl (2R)-2-aminopropanoate

There total 14 articles about benzyl (2R)-2-aminopropanoate 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: 76.5%

benzyl chloride (100-44-7) + rac-Ala-OH (302-72-7,25191-17-7,18875-37-1) → DL-alanine benzyl ester (17831-01-5,17831-02-6,46229-47-4)

Guidance literature:

rac-Ala-OH; With potassium carbonate; In acetone; at 35 ℃; for 0.5h;

benzyl chloride; With tetrabutylammomium bromide; In acetone; for 12h; Inert atmosphere;

Reference yield: 71.9%

3-[hydroxy[2-phenyl-1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphinyl]-2-(phenylmethyl)propanoic acid (207286-71-3) → Phenylmethyl N-[2-[[hydroxy[2-phenyl-1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphinyl]methyl]-1-oxo-3-phenylpropyl]-L-alaninate (207286-74-6) + DL-alanine benzyl ester (17831-01-5,17831-02-6,46229-47-4)

Guidance literature:

Reference yield: 70.0%

(+)-benzyl 2-(2-methoxyphenylamino)propionate (1352219-29-4) → D-alanine benzyl ester (17831-02-6)

Guidance literature:

With trichloroisocyanuric acid; sulfuric acid; In water; acetonitrile; at 0 - 25 ℃; for 3h; Inert atmosphere;

DOI:10.1021/ja2084493

upstream raw materials:

rac-Ala-OH

benzenesulfonic acid

benzyl alcohol

benzyl pyruvate

Downstream raw materials:

N-(bis-benzyloxy-phosphoryl)-alanine benzyl ester

benzyl pyruvate

benzyl 2-nitropropanoate

D-Alanine

Refernces

• 1、 Kitir, Betül,Baldry, Mara,Ingmer, Hanne,Olsen, Christian A.. "Total synthesis and structural validation of cyclodepsipeptides solonamide A and B". . p. 7721 - 7732. Retrieved 2014/12/10.
• 2、 Zhu, Shou-Fei,Xu, Bin,Wang, Guo-Peng,Zhou, Qi-Lin. "Well-defined binuclear chiral spiro copper catalysts for enantioselective N-H insertion". supporting information; experimental part. p. 436 - 442. Retrieved 2012/03/07.