Product Description

This dibenzoate-protected gemcitabine precursor is a critical intermediate for:

• Oncology Drug Synthesis: Key to manufacturing gemcitabine HCl (Gemzar®) and newer fluorinated analogs
• Controlled Functionalization: Selective deprotection allows further derivatization at the 5’- or 3’-position
• Enhanced Stability vs. Free Nucleoside: Benzoate groups prevent lactamization and improve shelf life

Structural Advantages:
✔ β-D-configuration for biological compatibility
✔ Geminal difluorines confer metabolic resistance (prolonged half-life)
✔ Cytosine N4-unprotected for direct phosphitylation in oligonucleotide synthesis

1. Product Identification

• IUPAC Name: 4-Amino-1-[(2R,3R,4R,5R)-3,5-bis(benzoyloxy)-4,4-difluoro-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
• CAS Number: 134790-39-9
• Molecular Formula: C₂₃H₂₀F₂N₃O₆
• Molecular Weight: 472.42 g/mol
• EC Number: 603-326-8
• Structural Confirmation:
  • 1H/13C NMR (DMSO-d₆) available
  • HRMS (ESI+): m/z 473.1432 [M+H]⁺

2. Quality Specifications

3. Physicochemical Properties

• Melting Point: 168–172°C (dec.)
• Specific Rotation: [α]²⁵D +72° ± 3° (c=1, DMF)
• Solubility:
  • Soluble: DMSO, DMF, pyridine
  • Moderately soluble: EtOAc, acetone
  • Insoluble: Water, hexanes
• LogD (pH 7.4): 1.9 ± 0.2
• Stability:
  • Stable for ≥3 years at –20°C (desiccated)
  • Degrades in aqueous solutions (hydrolysis at N-glycosidic bond above pH 8.0)

4. Product Applications

Pharmaceutical Manufacturing

• Gemcitabine API Synthesis:
  • Deprotection → Phosphorylation → Salt formation
• Novel Nucleoside Prodrugs:
  • 5’-Elongation for lipid conjugates (e.g., CP-4126)
  • 3’-Modifications for enhanced tumor targeting

Research Tools

• Fluorinated DNA Probes:
  • Incorporation into oligonucleotides for nuclease resistance studies
• Radiotracer Development:
  • Precursor for ¹⁸F-labeled PET imaging agents

5. Packaging & Storage

• Standard Packaging:
  • ≤10g: Amber glass vials with PTFE-lined caps
  • 10–500g: Double-sealed Al-foil bags with desiccant
  • >500g: Polyethylene drum (N₂ atmosphere)
• Storage Conditions:
  • Temperature: –20°C (long-term), 2–8°C (short-term)
  • Humidity: <30% RH (with molecular sieves)
  • Light Protection: Required (UV-sensitive)
• Shelf Life: 5 years when stored under recommended conditions

6. Safety & Handling

GHS Hazard Statements

• H302+H312+H332: Harmful if swallowed, in contact with skin, or inhaled
• H315: Causes skin irritation
• H319: Causes serious eye irritation

Precautions

• PPE: Nitrile gloves, lab coat, safety goggles
• Ventilation: Use fume hood for powder handling
• Spill Management: Absorb with inert material (silica gel), dispose as fluorinated waste

First Aid

• Skin Contact: Wash with 10% PEG-400 solution
• Eye Exposure: Rinse with saline (15 min)
• Ingestion: Administer activated charcoal (DO NOT induce vomiting)

Technical Support

• Scale-Up Services: Process optimization reports available
• Customization:
  • N4-protected variants (e.g., acetyl, benzoyl)
  • Isotope-labeled (¹⁵N, ¹³C) versions

Quality Documentation: Includes batch-specific CoA, HPLC chromatograms, and MSDS