1,2:4,5-Bis-O-(isopropylidene)-β-L-erythro-2,3-hexodiulo-2,6-pyranose
1,2:4,5-Bis-O-(isopropylidene)-β-L-erythro-2,3-hexodiulo-2,6-pyranose (CAS 198965-05-8), a chiral compound with the molecular formula C12H18O6, is a key reagent in asymmetric synthesis. It functions as both a reactant and a catalyst, notably in Shi epoxidation reactions. Its unique structure facilitates diastereoselective synthesis and the creation of complex molecules with biological activity, making it valuable in advanced organic chemistry research and development.
- IUPAC
- Shi epoxidation catalyst enantiomer
- Synonyms
- 3-hexodiulo-2,6-pyranoseC12H18O6
Diastereoselective Synthesis of α-Tocopherol
This compound serves as a critical reactant in the diastereoselective synthesis of α-tocopherol through Shi epoxidation. It enables precise control over stereochemistry in the formation of this vital antioxidant molecule.
Synthesis of Anticancer Agents
It is utilised in the synthesis of benzimidazole-based analogs of epothilone A, compounds exhibiting significant anticancer activity. This application highlights its role in medicinal chemistry research for novel therapeutic agents.
Preparation of Epothilone Analogs
As a catalyst, it is employed in the preparation of microtubule-stabilizing and antitumor active analogs of epothilone. This facilitates the development of potent antineoplastic drugs.
Synthesis of Natural Products
The compound is used in the synthesis of natural products such as (+)-aurilol, involving regio- and stereocontrolled ether ring formations. This showcases its utility in complex natural product synthesis.
| Molecular weight | 258.27 |
|---|---|
| Empirical formula | C12H18O6 |
| Optical activity | [α]22/D +111.0°, c = 0.5 in chloroform |
| Application | Reactant for:• Diastereoselective synthesis of a-tocopherol via Shi epoxidation1• Synthesis of benzimidazole-based analogs of epothilone A with anticancer activity2Catalyst for:• Preparation of microtubule-stabilizing and antitumor active analogs of epothilone3• Synthesis of (+)-aurilol via regio- and stereocontrolled A-D ether ring formations4 |
| Melting point | 98-104 °C |
Hazard statements
- H302Harmful if swallowed
| Water hazard class (WGK, DE) | 1 |
|---|---|
| Hazard codes (EU) | Xn |
| Risk statements (R) | 22 |
Hazard information is provided for guidance. Always consult the product Safety Data Sheet (SDS), available on request, before handling.
Documentation
Every batch ships with a Certificate of Analysis covering assay, identity and purity; the grade is confirmed against your enquiry. Safety Data Sheets and technical data sheets are available on request.
Supply & logistics
Samples for technical evaluation; bulk MOQ by grade and packaging. In-stock material ships in 7–10 working days, worldwide, with full export documentation.
What is 1,2:4,5-Bis-O-(isopropylidene)-β-L-erythro-2,3-hexodiulo-2,6-pyranose used for?
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This compound is primarily used as a reactant and catalyst in asymmetric synthesis, particularly for Shi epoxidation. It is instrumental in the diastereoselective synthesis of molecules like α-tocopherol and in the preparation of biologically active compounds including anticancer agents and natural products.
What is the CAS number and chemical formula for this product?
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The CAS number is 198965-05-8 and the chemical formula is C12H18O6.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies this chemical as a research-grade reagent. The specific purity and assay are available upon request. We do not represent this product as meeting USP, BP, or EP pharmacopoeia standards.
What are the primary safety concerns when handling this chemical?
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This chemical is classified with a GHS07 symbol and a Warning signal word. It carries the hazard statement H302, indicating it is harmful if swallowed. Appropriate personal protective equipment should be used, and it should be handled with care to avoid ingestion.
How is this chemical packed, shipped, and exported?
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As a specialist global supplier, Tech Serve Solutions ensures secure and compliant packaging for all shipments. We export this chemical worldwide, adhering to all relevant international shipping and customs regulations.
How can I request a sample or a quote?
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To request a sample or obtain a quotation, please contact our sales department directly through the website or via email, providing your specific requirements and delivery information.
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