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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

Signal Word

Warning

Hazard 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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Borman, S.
Chemical and Engineering News, 69(35), 11-11 (1991)
Ojima, I. et al.
Tetrahedron Letters, 34, 4149-4149 (1993)
Holton, R.A. et al.
Journal of the American Chemical Society, 116, 1597-1597 (1994)
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)
Kingston, D.G.I. et al.
Journal of Natural Products, 53, 1-1 (1990)

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