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Description
TCI D3661, (2S,3S)-(+)-2,3-Dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one, is a chiral building block belonging to the asymmetric synthesis group. The molecule is built on a seven-membered benzothiazepinone framework carrying two defined stereogenic centres at positions 2 and 3, together with a 4-methoxyphenyl substituent and a secondary hydroxyl group. This skeleton is the core framework of the benzothiazepine class, a structure widely recognised in medicinal chemistry, while the hydroxyl group and the free amide nitrogen provide two clear points of functionalisation. In the laboratory the material serves as an enantiomerically pure starting material for constructing benzothiazepine derivatives and as a reference compound in analytical work.
The characteristic that makes this compound the preferred choice is its established stereochemical purity, defined as the (2S,3S) configuration. In asymmetric synthesis, beginning from a material whose stereochemistry is already correct is far more efficient than constructing the chiral centres from scratch, because it removes the need for racemate resolution, for expensive chiral catalysts, and for the complicated chiral chromatographic purification that such routes normally demand. The positive optical rotation confirms the identity of the enantiomer, and the rigid bicyclic framework gives predictable geometry that carries through to subsequent transformations.
In Indonesian laboratories this type of chiral building block is typically used in university and institutional research groups working on asymmetric synthesis and medicinal chemistry, as well as in analytical and quality-control laboratories that need a defined stereochemical standard. Because the stereocentres are already set, the compound suits work programmes where chiral resolution capability is limited, allowing a synthetic route to proceed on a single-enantiomer basis from the first step onwards.
Laboratory Applications
- Benzothiazepine derivative synthesis — the seven-membered benzothiazepinone core is supplied intact, so researchers can proceed directly to derivatisation rather than assembling the ring system themselves.
- Asymmetric synthesis route development — the defined (2S,3S) configuration allows single-enantiomer routes to be planned without racemate resolution steps or expensive chiral catalyst screening at the outset.
- Selective functionalisation studies — the secondary hydroxyl group and the free amide nitrogen provide two clearly distinguishable reactive positions for controlled, stepwise chemical modification work.
- Analytical reference material — the compound serves as a reference standard in analytical work where a stereochemically defined benzothiazepine structure is required for identification or method verification.
- Medicinal chemistry structural exploration — the benzothiazepine skeleton is widely recognised in medicinal chemistry, making this building block suitable for structure-oriented exploratory synthesis around that framework.
Specifications
- Brand: TCI
- CAS Number: 42399-49-5
- Category: Chemistry > Asymmetric Synthesis > Chiral Building Blocks
- Chemical name: (2S,3S)-(+)-2,3-Dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one
- Stereochemistry: (2S,3S) configuration, positive optical rotation
- Pack sizes: available in standard TCI research-scale pack sizes; please confirm the required quantity when ordering
- Storage: store as indicated on the manufacturer's label and accompanying documentation
Handling and Storage
Store the container tightly closed in a cool, dry, well-ventilated place, away from direct sunlight, moisture, and incompatible chemicals, following the storage conditions stated on the manufacturer's label and safety data sheet. Keep the material in its original supplier container, or in a clean, chemically compatible and clearly labelled vessel if it must be transferred. Handle in a fume hood using standard laboratory protective equipment, including a lab coat, safety glasses, and suitable gloves. Avoid generating dust, avoid contact with skin and eyes, weigh out only the amount required, and reseal the container promptly to limit exposure to air and humidity. Dispose of residues and contaminated materials in accordance with institutional chemical waste procedures.
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