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(2R,3S)-N-Benzoyl-3-phenyl Isoserine

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(2R,3S)-N-Benzoyl-3-phenyl Isoserine manufacturers

(2R,3S)-N-Benzoyl-3-phenyl Isoserine Basic information
Product Name:(2R,3S)-N-Benzoyl-3-phenyl Isoserine
Synonyms:N-BENZOYL-(2R,3S)-3-AMINO-2-HYDROXY-3-PHENYL-PROPIONIC ACID;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
CAS:132201-33-3
MF:C16H15NO4
MW:285.3
EINECS:631-348-7
Product Categories:Herb extract;Serine Derivatives;Peptide Synthesis;Unnatural Amino Acid Derivatives;Amino Acids & Derivatives;Anti-virals;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
Mol File:132201-33-3.mol
(2R,3S)-N-Benzoyl-3-phenyl Isoserine Structure
(2R,3S)-N-Benzoyl-3-phenyl Isoserine Chemical Properties
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
pka3.40±0.17(Predicted)
color White to Off-White
Optical Rotation[α]20/D 40°, c = 1.0 in ethanol
Major Applicationpeptide synthesis
InChI1S/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
InChIKeyHYJVYOWKYPNSTK-UONOGXRCSA-N
SMILESO[C@H]([C@@H](NC(=O)c1ccccc1)c2ccccc2)C(O)=O
CAS DataBase Reference132201-33-3(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36
WGK Germany 3
HS Code 29242990
Storage Class11 - Combustible Solids
Hazard ClassificationsEye Irrit. 2
Skin Irrit. 2
STOT SE 3
MSDS Information
ProviderLanguage
SigmaAldrich English
(2R,3S)-N-Benzoyl-3-phenyl Isoserine Usage And Synthesis
Chemical PropertiesWhite 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.
UsesThe 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 suitabilityreaction type: solution phase peptide synthesis
(2R,3S)-N-Benzoyl-3-phenyl Isoserine Preparation Products And Raw materials
Tag:(2R,3S)-N-Benzoyl-3-phenyl Isoserine(132201-33-3) Related Product Information
Benzoyl peroxide L-Homoserine 3-(4-Hydroxyphenyl)propionic acid Folic acid Benzoyl chloride Ethyl 2-(Chlorosulfonyl)acetate D-Cycloserine L(+)-Lactic acid β-Alanine DL-Serine N-BENZOYL-(2R,3S)-3-PHENYLISOSERINE METHYL ESTER 7-Epitaxol Citric acid Chlorophosphonazo III 3,4'-Diaminodiphenylmethane L-alpha-Phosphatidylserines, brain, bovine Benzoyl isocyanate 10-Deacetylbaccatin III