L-Threonine Benzyl Ester Hydrochloride Chemical Properties

Melting point:

128.0 to 132.0 °C

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

powder to crystal

color 

White to Almost white

InChI

InChI=1/C11H15NO3.ClH/c1-8(13)10(12)11(14)15-7-9-5-3-2-4-6-9;/h2-6,8,10,13H,7,12H2,1H3;1H/t8-,10+;/s3

InChIKey

IDZGTFSDZJVMSD-YFYURQRANA-N

SMILES

C(OCC1=CC=CC=C1)(=O)[C@H]([C@H](O)C)N.[H]Cl |&1:10,11,r|

CAS DataBase Reference

33645-24-8

Safety Information

HS Code 

2922500090

L-Threonine Benzyl Ester Hydrochloride Usage And Synthesis

References

[1] Charles M, et al. Serine and Threonine Schiff Base Esters React with β-Anomeric Peracetates in the Presence of BF3·Et2O to Produce β-Glycosides. Journal of Carbohydrate Chemistry, 2010; 29.

Uses

L-threonine benzyl ester hydrochloride salt was reacted with the diaryl ketimine bis-(4-methoxyphenyl)-methenamine in CH3CN at rt to form the more nucleophilic L-threonine Schiff base (Benzyl N-bis (4-methoxyphenyl)methylene-L-threoninate) in excellent yield. In addition, L-threonine Schiff base, acting as glycosyl acceptor, reacted at rt with simple sugar peracetate donor with BF3·OEt2 promotion to provide the corresponding L-threonine O-linked glycosides in excellent yields and purities[1].

Preparation

The benzyl ester hydrochloride salt, L-Threonine Benzyl Ester Hydrochloride, was  prepared from L-threonine and PhCH2OH in the presence of p-toluenesulfonic acid[1]. Specifically, L-Threonine (4.0 g, 34 mmol) and pTsOH acid monohydrate (7.10 g, 38 mmol) were reacted with benzyl alcohol (40 mL) in 50 mL dry benzene using a Dean-Stark apparatus according to the procedure of Petursson and Bald-win. Yield:71.3%