| Identification | More | [Name]
N-Benzoyl-(2R,3S)-3-phenylisoserine | [CAS]
132201-33-3 | [Synonyms]
N-BENZOYL-(2R,3S)-3-AMINO-2-HYDROXY-3-PHENYL-PROPIONIC ACID
N-BENZOYL-(2R,3S)-3-PHENYLISOSERINE
TAXOL(R) SIDE CHAIN
(2R,3S)-3-Benzoylamino-2-Hydro
(2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropionacid
Taxol side chain alcohol
(2R, 3S)-3-BENZOYLAMINO-2-HYDROXY-3-PHENYLPROPIONACID,98+%
(2R,3S)-3-Benzoylamino-2-hydroxy-3-phenylpropionic acid
SIDE CHAINS OF PACLITAXEL--4
(2R,3S)-2-Hydroxy-3-(benzoylamino)-3-phenylpropionic acid
(2R,3S)-3-(Benzoylamino)-3-phenyl-2-hydroxypropanoic acid
(2R,3S)-N-Benzoylphenylisoserine | [EINECS(EC#)]
631-348-7 | [Molecular Formula]
C16H15NO4 | [MDL Number]
MFCD00274633 | [Molecular Weight]
285.29 | [MOL File]
132201-33-3.mol |
| Chemical Properties | Back Directory | [Melting point ]
169-172 °C (lit.) | [Boiling point ]
580.7±50.0 °C(Predicted) | [density ]
1.316±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Acetonitrile (Slightly), DMSO (Slightly), Ethanol (Slightly) | [form ]
Solid | [pka]
3.40±0.17(Predicted) | [color ]
White to Off-White | [Optical Rotation]
[α]20/D 40°, c = 1.0 in ethanol | [Major Application]
peptide synthesis | [InChI]
1S/C16H15NO4/c18-14(16(20)21)13(11-7-3-1-4-8-11)17-15(19)12-9-5-2-6-10-12/h1-10,13-14,18H,(H,17,19)(H,20,21)/t13-,14+/m0/s1 | [InChIKey]
HYJVYOWKYPNSTK-UONOGXRCSA-N | [SMILES]
O[C@H]([C@@H](NC(=O)c1ccccc1)c2ccccc2)C(O)=O | [CAS DataBase Reference]
132201-33-3(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P261-P264-P271-P280-P302+P352-P305+P351+P338 | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [HS Code ]
29242990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
White crystalline powder, soluble in methanol, ethanol, DMSO and other organic solvents. | [Uses]
(2R,3S)-N-Benzoyl-3-phenylisoserine is an intermediate in the preparation of potent anticancer drug Paclitaxel (P132500) used to study the location of the binding sites. (2R,3S)-N-Benzoyl-3-phenylisoserine shows cytotoxic, antiviral and immunomodulatory activity. | [Uses]
The presence of this chiral side chain has proven to be essential for the biological activity of taxol, one of the most promising anticancer agents being investigated. The challenging synthesis of taxol has stimulated interest in the attachment of the C-13 side chain to naturally derived taxanes like baccatin III. | [reaction suitability]
reaction type: solution phase peptide synthesis |
|
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