444375
N-Benzoyl-(2R,3S)-3-phenylisoserine
98%
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About This Item
Linear Formula:
C6H5CONHCH(C6H5)CH(OH)CO2H
CAS Number:
Molecular Weight:
285.29
MDL number:
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.22
Quality Level
Assay
98%
optical activity
[α]20/D −40°, c = 1.0 in ethanol
reaction suitability
reaction type: solution phase peptide synthesis
mp
169-172 °C (lit.)
application(s)
peptide synthesis
SMILES string
O[C@H]([C@@H](NC(=O)c1ccccc1)c2ccccc2)C(O)=O
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
InChI key
HYJVYOWKYPNSTK-UONOGXRCSA-N
Related Categories
Application
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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E K Rowinsky et al.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology, 9(9), 1692-1703 (1991-09-01)
Untreated and minimally pretreated solid tumor patients received alternating sequences of taxol and cisplatin. Sequential dose escalation of each agent using taxol doses of 110 or 135 mg/m2 and cisplatin doses of 50 or 75 mg/m2 resulted in four dosage
Mangatal, L. et al.
Tetrahedron, 45, 4177-4177 (1989)
Holton, R.A. et al.
Journal of the American Chemical Society, 116, 1597-1597 (1994)
Ojima, I. et al.
Tetrahedron Letters, 34, 4149-4149 (1993)
Taxol: twenty years later, the story unfolds.
E K Rowinsky et al.
Journal of the National Cancer Institute, 83(24), 1778-1781 (1991-12-18)
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