benzyl (2S,3R)-2-((tert-butoxycarbonyl)amino)-3-hydroxy-3-(4-methoxyphenyl)propanoate

Benzyl (2S,3R)-2-((tert-butoxycarbonyl)amino)-3-hydroxy-3-(4-methoxyphenyl) propanoate – What makes it unique? Racemic or low‑ee intermediates often generate inseparable diastereomeric impurities during API synthesis, driving up purification costs and reducing yields. In contrast, benzyl (2S,3R)-2-((tert-butoxycarbonyl)amino)-3-hydroxy-3-(4-methoxyphenyl) propanoate is delivered with a fixed (2S,3R) configuration and ≥99% ee, validated by chiral HPLC and optical rotation. benzyl (2S,3R)-2-((tert-butoxycarbonyl)amino)-3-hydroxy-3-(4-methoxyphenyl) propanoate enables direct use in convergent drug syntheses without time‑consuming chiral resolution. Moreover, the Boc group and benzyl ester are orthogonal protecting handles that can be selectively removed under mild acidic or hydrogenolytic conditions, allowing rapid assembly of complex pharmacophores. For these reasons, benzyl (2S,3R)-2-((tert-butoxycarbonyl)amino)-3-hydroxy-3-(4-methoxyphenyl)propanoate is the preferred chiral building block for scale‑up campaigns requiring stereochemical integrity.

Applications

This intermediate is a key building block for protease inhibitors, antiviral candidates, and other chiral drugs containing a β‑hydroxyphenylalanine scaffold. The 4‑methoxyphenyl group can serve as a hydrophobic aromatic probe in SAR studies. Meanwhile, the Boc group is cleaved under mild acidic conditions, and the benzyl ester can be selectively removed via hydrogenolysis or saponification — a true orthogonal protection strategy for peptide modification or cyclization reactions.

Product Parameters

Key Applications

1. Asymmetric Synthesis

With its pre-built (2S,3R) adjacent chiral centers, this intermediate can be used directly in Staudinger cyclizations, Mitsunobu reactions, or metal-catalyzed cross-couplings while preserving configuration. Outsourcing the chiral resolution step to Cosperpharm reduces your process development risk.

2. Peptide Mimetics & Cyclic Peptides

The Boc-protected amino group is ready for coupling with carboxylic acids, while the benzyl ester can be removed last for cyclization – ideal for conformationally constrained cyclic peptides. The 4-methoxyphenyl group improves lipophilicity and blood-brain barrier penetration for CNS targets.

3. Reference Standard for Impurity Control

For companies developing related APIs, this intermediate can serve as a process impurity standard or degradation marker. We offer ultra-pure vials (≥99.5%) with full structural authentication (NMR, HRMS, IR).

Frequently Asked Questions (FAQ)

Q1: How do you guarantee the enantiomeric purity?

A: We control stereochemistry from the asymmetric synthesis step. The final product is tested by chiral HPLC using a certified reference standard of known configuration. Each batch includes a chiral chromatogram and specific rotation data. For customers requiring ≥99.5% ee, we offer one recrystallization as a custom service.

Q2: Will the compound racemize or degrade during storage?

A: It is stable at 2‑8 °C in sealed, dark containers. Forced degradation studies show no racemization after 30 days at 25 °C open to air, though trace hydrolysis (benzyl ester opening) or Boc deprotection may occur. To avoid this, allow the bottle to warm to room temperature before opening and handle under inert gas. For frequent use, we can supply pre‑aliquoted vials (1 g or 5 g) under nitrogen.

Contact us

Ready to purchase benzyl (2S,3R)-2-((tert-butoxycarbonyl)amino)-3-hydroxy-3-(4-methoxyphenyl)propanoate? Contact Cosperpharm today for a sample or quote. Whether you need high-purity reference standards for drug impurity testing, research-grade material for drug discovery, or custom synthesis for large-scale production