(5R-cis)-Toluene-4-sulfonic acid 5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-yl)methyltetrahydrofuran-3-ylmethyl ester
[CAS# 149809-43-8]

Identification

• Classification: Pharmaceutical intermediate >> API intermediate
• Name: (5R-cis)-Toluene-4-sulfonic acid 5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-yl)methyltetrahydrofuran-3-ylmethyl ester
• Synonyms: [(3S,5R)-5-(2,4-difluorophenyl)-5-(1,2,4-triazol-1-ylmethyl)oxolan-3-yl]methyl 4-methylbenzenesulfonate
• Molecular Formula: C₂₁H₂₁F₂N₃O₄S
• Molecular Weight: 449.47
• CAS Registry Number: 149809-43-8
• SMILES: CC1=CC=C(C=C1)S(=O)(=O)OC[C@H]2C[C@](OC2)(CN3C=NC=N3)C4=C(C=C(C=C4)F)F

Properties

• Solubility: 1.768 mg/L (25 °C water)
• Density: 1.4±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.616, Calc.^*
• Melting point: 229.35 °C
• Boiling Point: 608.1±65.0 °C (760 mmHg), Calc.^*, 535.86 °C
• Flash Point: 321.6±34.3 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software

Discovery and Applications

The chemical compound known as "(5R-cis)-Toluene-4-sulfonic acid 5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-yl)methyltetrahydrofuran-3-ylmethyl ester" is commonly referred to as "voriconazole." It was discovered in the late 20th century by researchers at Pfizer as part of a program aimed at developing new antifungal agents.

(5R-cis)-Toluene-4-sulfonic acid 5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-yl)methyltetrahydrofuran-3-ylmethyl ester is a broad-spectrum antifungal medication used in the treatment of invasive fungal infections. It belongs to the azole class of antifungals and works by inhibiting the synthesis of ergosterol, a crucial component of fungal cell membranes. Voriconazole is indicated for the treatment of invasive aspergillosis, candidiasis, and certain other serious fungal infections, particularly in immunocompromised patients. It is available in both oral and intravenous formulations and is considered a first-line treatment for many life-threatening fungal infections due to its broad spectrum of activity, favorable pharmacokinetics, and clinical efficacy. Additionally, voriconazole has been used prophylactically in high-risk patients to prevent invasive fungal infections associated with certain medical procedures or conditions.

References

2017. {(3S,5R)-5-(2,4-Difluorophenyl)-5-[(1H-1,2,4-triazol-1-yl)