Cbz-L-Threonine benzyl ester Chemical Properties

Melting point:

78-82°C

Boiling point:

536.8±50.0 °C(Predicted)

Density 

1.228±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,2-8°C

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

pka

10.76±0.46(Predicted)

form 

powder to crystal

color 

White to Almost white

optical activity

Consistent with structure

CAS DataBase Reference

16597-50-5(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

HS Code 

29224999

MSDS

• Language:English Provider:ALFA

Cbz-L-Threonine benzyl ester Usage And Synthesis

Chemical Properties

White powder

Synthesis

General procedure for the synthesis of compounds (CAS: 84500-41-4) from (2S,3R)-2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoic acid and benzyl bromide: (2S,3R)-2- benzyloxycarbonylamino-3-hydroxybutanoic acid (1.0 g, 4.0 mmol) was dissolved in a mixture of N,N-dimethylformamide (DMF, 15.0 mL) and deionized water (5.0 mL) in a mixed solvent, cesium carbonate (644.5 mg, 2.0 mmol) was added, and the reaction was stirred for 30 min at room temperature. After the reaction was completed, the reaction solution was concentrated and the residual water was removed by azeotropy with toluene (3 × 10 mL). Subsequently, a solution of benzyl bromide (0.71 mL, 5.9 mmol) in DMF (10.0 mL) was added to the dried residue and the reaction was continued for 24 hours. At the end of the reaction, the reaction was quenched by the addition of water (15 mL) and extracted with ethyl acetate (2 x 30 mL). The organic phases were combined, dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by fast column chromatography with ethyl acetate/hexane (1:3, v/v) as eluent to give the target compound (1.149 g, 84% yield) as a white powder. The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3), 13C NMR (125 MHz, CDCl3) and LC-ESI-MS: 1H NMR (400 MHz, CDCl3) δ 7.26-6.35 (m, 10H), 5.60 (d, 1H, J = 8.7 Hz), 5.17-5.24 (m, 2H) 5.13 (s, 2H), 4.37-4.39 (m, 2H), 1.97 (br, 1H), 1.63 (br, 1H), 1.23 (d, 1H, J = 6.3 Hz); 13C NMR (125 MHz, CDCl3) δ 171.2, 156.9, 136.2, 135.3, 128.6, 128.5, 128.5 128.5, 128.2, 128.0, 68.0, 67.4, 67.2, 59.5, 19.9; LC-ESI-MS [M + H]+ C19H21NO5 Calculated value 344.14, measured value 344.03.

References

[1] Tetrahedron Letters, 1968, p. 6323 - 6326
[2] Tetrahedron, 2018, vol. 74, # 23, p. 2891 - 2903

Cbz-L-Threonine benzyl ester(16597-50-5)Related Product Information

• N-Carbobenzyloxy-L-threonine methyl ester
• Benzyl benzoate
• L-Threonine
• Methyl acrylate
• Benzyl nicotinate
• Benzyl alcohol
• Benzyl chloride
• Tris(trimethylsilyl)phosphate
• Benzyl chloroformate
• N-Cbz-L-Threonine
• Z-Thr-OEt
• Z-THR(TBU)-OME
• Z-L-THREONINOL
• Z-THR-OSU
• Benzyl (2R,3S)-(1-carbamoyl-2-hydroxypropyl)carbamate
• Z-PHG-OH
• Z-TRP-OSU
• Z-PRO-NH2