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Key Documents

444375

Sigma-Aldrich

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

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.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Mangatal, L. et al.
Tetrahedron, 45, 4177-4177 (1989)
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)
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
Holton, R.A. et al.
Journal of the American Chemical Society, 116, 1597-1597 (1994)

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