Methyl (2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoate

Methyl (2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoate is an N-benzoylated phenylisoserine ester used in paclitaxel side-chain chemistry. It supplies the stereodefined amino-hydroxy framework and the benzamido substituent characteristic of that side chain. The methyl ester protects the carboxyl group, while the free hydroxyl provides a separate site for temporary protection.

The selected material is the methyl ester rather than the corresponding free acid or a taxane-bound derivative. Synthetic routes can manipulate the hydroxyl and convert the ester into a coupling-ready acid derivative while retaining the benzamido group. Its value is therefore in transferring an already assembled chiral side-chain fragment into later taxane operations, rather than providing the biological action of paclitaxel itself.

Typical Applications

• Paclitaxel side-chain acid preparation: Used in ester-conversion sequences that generate the corresponding N-benzoyl phenylisoserine acid or protected acid derivative for subsequent esterification at the taxane C13 position.
• Hydroxyl-protected side-chain intermediates: Used to prepare protected phenylisoserine derivatives in which the secondary alcohol is masked during activation and coupling, then restored later in the paclitaxel synthesis sequence.

Specifications

Specifications describe the standard grade. Tolerance, test method and documentation package are confirmed per order.