| Identification | Back Directory | [Name]
N-Carbobenzoxy-L-homoserine | [CAS]
35677-88-4 | [Synonyms]
Cbz-hse-OH
Cbz-Homoserine
Cbz-L-Homoserine
N-Carbobenzoxy-L-homoserine
N-(Benzyloxycarbonyl)-L-homoserine
Cbz-HoMoser Cbz-HoMoserine Cbz-Hse
(S)-benzyl 2-amino-4-hydroxybutanoate
L-HoMoserine, N-[(phenylMethoxy)carbonyl]-
2-CarboxyaMino-4-hydroxybutyric acid, N-benzyl Ester
(2S)-4-hydroxy-2-(phenylmethoxycarbonylamino)butanoic
(2S)-4-hydroxy-2-(phenylmethoxycarbonylamino)butanoicaci
(S)-2-(((Benzyloxy)carbonyl)amino)-4-hydroxybutanoic acid
(2S)-2-{[(benzyloxy)carbonyl]amino}-4-hydroxybutanoic acid
(2S)-4-hydroxy-2-(phenylmethoxycarbonylamino)butanoic acid | [Molecular Formula]
C12H15NO5 | [MDL Number]
MFCD00056718 | [MOL File]
35677-88-4.mol | [Molecular Weight]
253.25 |
| Chemical Properties | Back Directory | [Melting point ]
100-101 °C | [Boiling point ]
519.9±50.0 °C(Predicted) | [density ]
1.311 | [storage temp. ]
2-8°C | [form ]
Solid | [pka]
3.85±0.10(Predicted) | [color ]
White to off-white | [Optical Rotation]
Consistent with structure |
| Hazard Information | Back Directory | [Uses]
N-Carbobenzoxy-L-homoserine (cas# 35677-88-4) is a compound useful in organic synthesis. | [Synthesis]
General procedure for the synthesis of (S)-2-(((benzyloxy)carbonyl)amino)-4-hydroxybutyric acid from L-homoserine and benzyl chloroformate: L-homoserine (4.76 g, 40 mmol) was dissolved in a solvent mixture of H2O (200 mL) and 1,4-dioxane (50 mL). To this solution was added NaHCO3 (13.44 g, 160 mmol), followed by slow dropwise addition of benzyl chloroformate (6.76 mL, 48 mmol). The reaction mixture was stirred at room temperature overnight. After completion of the reaction, the mixture was washed twice with ethyl acetate (EA). The aqueous layer was neutralized to pH 2 with 4 mol/L HCl solution and then extracted with EtOAc. The organic layers were combined, washed sequentially with water and brine, dried over anhydrous Na2SO4 and concentrated to dryness under reduced pressure. The resulting crude product (8.86 g, 35 mmol, 87.5% yield) was used directly in the next reaction without further purification. | [References]
[1] Synthetic Communications, 1988, vol. 18, # 14, p. 1715 - 1722
[2] Journal of Organic Chemistry, 2003, vol. 68, # 7, p. 2668 - 2672
[3] Tetrahedron Letters, 2017, vol. 58, # 42, p. 3970 - 3973
[4] Journal of Medicinal Chemistry, 2015, vol. 58, # 23, p. 9133 - 9153
[5] Journal of Organic Chemistry, 1986, vol. 51, # 26, p. 5047 - 5050 |
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