Methyl (2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoate

Methyl (2R,3S)-N-Boc-3-phenylisoserinate is a protected amino-hydroxy ester used in docetaxel side-chain synthesis. It delivers the stereodefined phenylisoserine framework and the tert-butoxycarbonyl group on nitrogen. The methyl ester provides a protected carboxyl function, while the secondary alcohol remains available for selective protection or further synthetic conversion.

The N-Boc substituent differentiates this intermediate from the N-benzoyl analogue used in paclitaxel chemistry. Here, the carbamate is part of the intended docetaxel side-chain structure rather than simply a group that must always be removed. Routes built from this material can convert the ester into a side-chain acid and control the hydroxyl independently before attachment to the taxane core.

Typical Applications

• Docetaxel side-chain acid synthesis: Used to obtain the N-Boc phenylisoserine carboxylic-acid fragment through methyl-ester conversion, retaining the side-chain configuration and nitrogen carbamate.
• Protected taxane esterification intermediates: Used in sequences that protect the side-chain hydroxyl and prepare an activated acid derivative for coupling to a suitably functionalized taxane nucleus.

Specifications

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