TCI
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Description
(S)-Glycidyl Trityl Ether is the enantiomer of the (R) form and a glycidol derivative in the (S) configuration whose primary hydroxyl group is protected as a trityl ether. In the laboratory this compound serves as a ready-to-use chiral building block that already carries its protecting-group strategy in place, allowing a reaction sequence to be directed immediately at the epoxide ring rather than spending steps on installing protection. Because it arrives with defined stereochemistry, it lets chemists introduce a single, known chiral centre at the very start of a synthetic route.
The availability of both enantiomers gives researchers the freedom to assemble a pair of mirror-image target compounds, a requirement that is common in structure-activity relationship studies and in drug candidate development. The characteristics that make this compound a preferred choice are centred on the trityl group: it is sterically bulky, stable across a wide range of reaction conditions, yet removable under mildly acidic conditions, which makes it orthogonal to many other protecting groups. The steric volume of this group can also direct nucleophilic attack on the oxirane ring, helping to achieve the desired regioselectivity.
This compound is generally supplied as a crystalline solid, which makes accurate weighing straightforward, allows purification by recrystallisation, and makes it more convenient to store and handle than glycidyl ethers of other physical forms. In Indonesian laboratories these practical qualities matter, and the material is typically used in academic and industrial research groups working on asymmetric synthesis, where a reliably handled solid chiral building block supports reproducible small-scale work.
Laboratory Applications
- Asymmetric synthesis route development: the defined (S) configuration introduces a known stereocentre at the outset, so the resulting stereochemistry of downstream products can be traced back to a single controlled starting point.
- Enantiomer pair preparation for structure-activity relationship studies: because both the (R) and (S) forms are available, matched mirror-image target compounds can be prepared under otherwise identical synthetic conditions.
- Drug candidate development work: the compound supplies a chiral fragment with its primary hydroxyl already protected, shortening the route and reducing the number of protection and deprotection operations required.
- Regioselective epoxide ring opening: the bulky trityl group sterically influences where nucleophiles attack the oxirane ring, which helps chemists steer the reaction toward the desired regiochemical outcome.
- Orthogonal protecting-group strategies: the trityl ether withstands many reaction conditions yet is cleaved under mild acid, so it can be removed selectively while other protecting groups in the molecule remain intact.
Specifications
- Brand: TCI
- CAS number: 129940-50-7
- Category: Chemistry > Asymmetric Synthesis > Chiral Building Blocks
- Pack sizes: available in the pack sizes listed for this catalogue item
- Physical form: generally a crystalline solid
- Storage: store according to the conditions stated on the manufacturer's label and safety data sheet
Handling and Storage
Store this compound in its original tightly closed container, kept in a cool, dry and well-ventilated place away from heat, direct sunlight and moisture, and follow the storage conditions stated on the manufacturer's label and safety data sheet. Keep the container closed when not in use to protect the material from atmospheric moisture. As a crystalline solid it is convenient to weigh and transfer, and handling is best carried out with clean, dry spatulas and glassware to avoid contamination. Because the epoxide ring is a reactive functional group, avoid contact with strong acids, strong bases and nucleophilic reagents during storage. Handle in a fume hood using standard laboratory personal protective equipment, including a lab coat, safety glasses and suitable gloves, and consult the safety data sheet before use.
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