(1S-trans)-2-[(Phenylmethoxy)methyl]-3-cyclopenten-1-ol
CAS 110567-21-0
CAS · 110567-21-0
Product Overview
(1S-trans)-2-[(Phenylmethoxy)methyl]-3-cyclopenten-1-ol is a high-purity pharmaceutical-intermediates supplied for industrial and specialty chemical applications. Contact our team for specifications, packaging options and lead times.
Product Specifications
| Appearance | Brown to tan oily matter |
|---|---|
| Purity | 95.0% min |
| Identification | The retention time of major peak in the chromatogram of the sample solution corresponds to that in the chromatogram of the standard solution |
| Impurity R1 (RRT≈0.40) | 1.0% max |
| Impurity D1 (RRT≈1.25) | 1.0% max |
| Total impurity | 5.0% max |
| Enantiomer | 1.5% max |
| Water | 1.0% max |
Applications
Pharmaceutical Intermediate in Entecavir Production
This compound is a crucial chiral intermediate in the multi-step synthesis of Entecavir, a carbocyclic nucleoside analog approved for the treatment of chronic hepatitis B.
It provides the cyclopentyl scaffold with the correct stereochemistry, which is essential for the biological activity of the final drug molecule.
Carbocyclic Nucleoside Synthesis
Used in preparing a variety of carbocyclic deoxyguanosine analogs, which possess antiviral properties against DNA viruses such as hepatitis B virus (HBV) and herpes viruses.
Specialty Chemical Research
Employed in academic and industrial R&D for designing novel cyclopentyl alcohol derivatives, potentially leading to new classes of nucleoside analog drugs.
Functions as a reference material for stereochemical studies in asymmetric synthesis.
Custom Chemical Synthesis
Serves as a modular building block for structure–activity relationship (SAR) studies, enabling medicinal chemists to modify functional groups while retaining the cyclopentyl backbone.
Can be transformed into a variety of protected or functionalized intermediates for drug development pipelines.
Benefits
Defined Chiral Stereochemistry
Exists in the (1S-trans) configuration, which ensures precise three-dimensional orientation for target drug structures.
Reduces the need for post-synthesis chiral resolution, saving production time and improving yield.
High Synthetic Versatility
Contains both hydroxyl and benzyloxymethyl groups, which can participate in a broad range of chemical transformations (oxidation, protection/deprotection, substitution, coupling).
Compatible with common protecting group strategies in multi-step organic synthesis.
Purity and Reliability
Available in research and commercial grades with purity ≥98–99%, allowing for consistent reaction performance and predictable outcomes.
Stability under standard laboratory conditions enables long-term storage without significant degradation.
Enabling Efficient Drug Manufacture
Shortens the synthetic route toward Entecavir and similar molecules by introducing a pre-functionalized cyclopentyl core early in the synthesis.
Facilitates scalable production due to reproducible reaction yields.
Broad Research Impact
Contributes to medicinal chemistry innovations by enabling the creation of novel cyclopentyl derivatives for antiviral screening.
Supports patentable synthetic pathways and intellectual property development in the pharmaceutical sector.
Conclusion
(1S-trans)-2-[(Phenylmethoxy)methyl]-3-cyclopenten-1-ol (CAS 110567-21-0) is a high-value chiral building block, primarily recognized for its role in the synthesis of Entecavir, a key hepatitis B antiviral. Its well-defined stereochemistry, multifunctional groups, and compatibility with diverse synthetic methodologies make it an indispensable intermediate in antiviral drug research and production. Beyond its primary pharmaceutical application, it serves as a versatile tool for medicinal chemists seeking to develop next-generation carbocyclic nucleosides and related therapeutic agents. Its purity, stability, and synthetic flexibility collectively ensure its importance in both industrial manufacturing and cutting-edge research.
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