N-Carbobenzyloxy-L-threonine methyl ester Chemical Properties

Melting point:

92-94 °C(lit.)

alpha 

-18 º (c=1, MeOH)

Boiling point:

410.46°C (rough estimate)

Density 

1.2100 (rough estimate)

refractive index 

1.4365

storage temp. 

Sealed in dry,Store in freezer, under -20°C

form 

Powder

pka

10.79±0.46(Predicted)

color 

White

optical activity

[α]25/D 18°, c = 1 in methanol

Water Solubility 

miscible

BRN 

2220800

CAS DataBase Reference

57224-63-2(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

N-Carbobenzyloxy-L-threonine methyl ester Usage And Synthesis

Chemical Properties

white to off-white powder

Uses

peptide synthesis

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

In a 2L beaker, 100 g of L-threonine methyl ester hydrochloride was dissolved in 600 ml of water and the pH was adjusted to a suitable range using sodium bicarbonate. Subsequently, 110 g of benzyl chloroformate (Z-Cl) was slowly added dropwise and the pH of the reaction system was kept between 8-9, which was adjusted using 2 M sodium hydroxide solution. After completion of the reaction, 1 L of ethyl acetate was added for extraction. The organic phase was washed sequentially with 500 ml of water and 500 ml of saturated saline, and then dried with 100 g of anhydrous sodium sulfate. After filtration, it was concentrated to dryness under reduced pressure to obtain a solid product. The solid was dissolved in 600 ml of a suitable solvent for crystallization, filtered and dried to give 140 g of N-benzyloxycarbonyl-L-threonine methyl ester (Z-Thr-OMe) in 89.1% yield.

References

[1] Patent: CN106631900, 2017, A. Location in patent: Paragraph 0015
[2] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 24, p. 3697 - 3703
[3] Justus Liebigs Annalen der Chemie, 1962, vol. 656, p. 190 - 204
[4] Journal of Organic Chemistry, 1985, vol. 50, # 23, p. 4515 - 4523
[5] Patent: WO2010/17060, 2010, A1. Location in patent: Page/Page column 44-45

N-Carbobenzyloxy-L-threonine methyl ester(57224-63-2)Related Product Information

• Methyl acetate
• Kresoxim-methyl
• Methyl acrylate
• Methylparaben
• Bensulfuron methyl
• L-Threonine
• METHYL THIOPHENE-2-CARBOXYLATE
• Cbz-L-Threonine benzyl ester
• Benzyl (2R,3S)-(1-carbamoyl-2-hydroxypropyl)carbamate
• Z-THR(BZL)-OH
• Z-Thr-OEt
• Thiophanate-methyl
• Z-THR(TBU)-OME
• Methyl
• N-Cbz-L-Threonine
• Z-L-THREONINOL
• Z-THR-OSU
• Z-TYR-NH2