Introduction
In modern pharmaceutical manufacturing, chiral intermediates serve as the indispensable “molecular building blocks” for constructing numerous blockbuster drugs. Today, we turn the spotlight on a structurally compact yet widely applied chiral small molecule — (S)-3-Hydroxytetrahydrofuran ((S)-(+)-3-Hydroxytetrahydrofuran). Unassuming as it may appear, this compound plays a pivotal role in the synthetic routes of multiple blockbuster drugs across oncology, diabetes, and antiviral therapies. Let’s take a closer look at this “star molecule.”
| Parameter | Value |
|---|---|
| CAS Number | 86087-23-2 |
| Molecular Formula | C₄H₈O₂ |
| Molecular Weight | 88.11 |
| EINECS Number | 425-090-2 |
| HS Code | 29321900 |
| SMILES | O[C@H]1CCOC1 |
| Property | Value |
|---|---|
| Appearance | Colorless to pale yellow transparent liquid |
| Density (25°C) | 1.103 g/mL |
| Boiling Point (15 mmHg) | 80°C |
| Refractive Index (n20/D) | 1.45 |
| Flash Point | 79°C (175°F) |
| Specific Rotation [α]20/D | +17.5° (c = 2.4, MeOH) |
| Vapor Pressure (25°C) | 47 Pa |
| LogP | −0.784 (22°C, pH 6.8) |
| pKa (predicted) | 14.49 ± 0.20 |
| Water Solubility | Soluble |
Applications
The reason (S)-3-hydroxytetrahydrofuran is dubbed a “star molecule” lies fundamentally in its role as a chiral intermediate widely incorporated into the synthesis of multiple blockbuster drugs. The principal application areas include:
1. Anticancer Drug — Afatinib
Afatinib, developed by Boehringer Ingelheim, is a second-generation irreversible ErbB family blocker used as first-line treatment for EGFR mutation-positive advanced non-small cell lung cancer (NSCLC) and for HER2-positive advanced breast cancer. (S)-3-Hydroxytetrahydrofuran serves as the key building block for the tetrahydrofuran oxy moiety in the afatinib molecule.
According to market research, the global afatinib market was valued at approximately USD 970 million in 2024 and is projected to reach USD 1.49 billion by 2032, growing at a CAGR of about 6.3%. Notably, EGFR mutation rates in Asian populations range from 30% to 50% (compared to only 10–15% in Western populations), indicating sustained strong demand for afatinib and its intermediates in the Chinese market.
2. Antidiabetic Drug — Empagliflozin
Empagliflozin, co-developed by Boehringer Ingelheim and Eli Lilly, is an SGLT-2 inhibitor and the first antidiabetic drug demonstrated to reduce cardiovascular death risk in type 2 diabetes patients. Its indications have since expanded to include heart failure and chronic kidney disease.
(S)-3-Hydroxytetrahydrofuran is an important chiral building block in the empagliflozin synthesis route. In terms of market performance, empagliflozin is a “mega-blockbuster” — global sales exceeded USD 10 billion in 2023 and are projected to reach USD 14–15 billion by 2025. The global SGLT-2 inhibitor market was valued at approximately USD 18.18 billion in 2025 and is expected to grow to USD 33.11 billion by 2035. In China, empagliflozin has grown from RMB 1.2 billion in 2019 to over RMB 11 billion in 2025, representing a compound annual growth rate exceeding 50%.
3. Anti-HIV Drug — Amprenavir and Fosamprenavir
Amprenavir is a second-generation HIV protease inhibitor, and fosamprenavir calcium is its prodrug form. (S)-3-Hydroxytetrahydrofuran is a key chiral intermediate in the synthesis of amprenavir, providing the critical furan oxy pharmacophore in the molecule.
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