| Identification | More | [Name]
Z-SER(BZL)-OH | [CAS]
20806-43-3 | [Synonyms]
BENZYLOXYCARBONYL-O-BENZYL-L-SERINE
CBZ-SER(BZL)-OH
N-ALPHA-CARBOBENZOXY-O-BENZYL L-SERINE
N-ALPHA-CBZ-O-BENZYL-L-SERINE
N-CARBOBENZOXY-O-BENZYL-L-SERINE
Z-O-BENZYL-L-SERINE
Z-SER(BZL)-OH
Z-SERINE(BZL)-OH
N-(benzyloxycarbonyl)-O-benzyl-L-serine
Cbz-O-benzyl-L-serine
N-alpha-Benzyloxycarbonyl-O-benzyl-L-serine
Z-L-Ser(Bzl)-OH
N-(Benzyloxycarbonyl)-O-benzylserine
N-Cbz-O-Benzyl-L-Ser-OH | [EINECS(EC#)]
244-049-8 | [Molecular Formula]
C18H19NO5 | [MDL Number]
MFCD00022029 | [Molecular Weight]
329.35 | [MOL File]
20806-43-3.mol |
| Chemical Properties | Back Directory | [Boiling point ]
537.1±50.0 °C(Predicted) | [density ]
1.253±0.06 g/cm3(Predicted) | [storage temp. ]
Store at RT. | [solubility ]
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | [form ]
Powder | [pka]
3.51±0.10(Predicted) | [color ]
White to off-white | [Optical Rotation]
Consistent with structure | [Water Solubility ]
Slightly soluble in water. | [CAS DataBase Reference]
20806-43-3(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Uses]
Cbz-Ser(Bzl)-OH is used in preparation of Aminoamide derivatives as anticancer agents. | [Synthesis]
At room temperature, O-benzyl-L-serine (25.0 g, 128 mmol) was dissolved in a mixed solvent of water (200 mL) and dioxane (100 mL) and sodium carbonate (7.46 g, 70 mmol) was added. Subsequently, a solution of dibenzyl dicarbonate (36.1 g, 126 mmol) in dioxane (100 mL) was slowly added dropwise and the reaction mixture was stirred at room temperature for 18 hours. Upon completion of the reaction, the dioxane was removed by vacuum evaporation and the remaining aqueous phase was extracted with ether. The organic phases were combined, dried over anhydrous sodium sulfate and concentrated under vacuum to give the crude product N-benzyloxycarbonyl-O-benzyl-L-serine (39.57 g, 95% yield) as a white solid, which was finally purified by washing with hexane. | [References]
[1] Liebigs Annalen der Chemie, 1994, # 6, p. 641 - 644
[2] Patent: US5030654, 1991, A
[3] Patent: EP274234, 1991, B1 |
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