(−)-2,3-O-Isopropylidene-D-erythronolactone
(−)-2,3-O-Isopropylidene-D-erythronolactone (CAS 25581-41-3) is a chiral synthon with the molecular formula C7H10O4 and a molecular weight of 158.15 g/mol. This compound is valuable in carbohydrate chemistry and chemical synthesis, particularly for constructing complex molecules. It undergoes Aldol condensations and is employed in the synthesis of various biologically relevant structures, including indolizidines and segments of natural products like calyculin.
- Synonyms
- C7H10O4
Aldol Condensation Reactions
(−)-2,3-O-Isopropylidene-D-erythronolactone effectively participates in Aldol condensations, particularly with silyl ketene acetals. This reactivity makes it a useful building block for introducing specific stereochemistry into carbon chains.
Spiroannulated Carbohydrate Synthesis
This compound serves as a key chiral intermediate in the synthesis of spiroannulated carbohydrate structures. These complex architectures are of interest in medicinal chemistry and glycobiology research.
Synthesis of Natural Product Segments
It has been employed in convergent synthetic strategies to build segments of complex natural products. Examples include the synthesis of hydroxylated indolizidines and the oxazole portion of the potent cytotoxin calyculin.
Preparation of Functionalised Benzoquinones
The synthon has been utilised in the synthesis of carbohydrate-substituted benzoquinones. These compounds can possess interesting biological activities and are valuable in chemical biology studies.
| Molecular weight | 158.15 |
|---|---|
| Empirical formula | C7H10O4 |
| Assay | 98% |
| Optical activity | [α]20/D −118°, c = 1 in H2O |
| Application | Undergoes Aldol condensations with silyl ketene acetals.1 Employed in spiroannulated carbohydrate synthesis.2 Convergent syntheses of a hydroxylated indolizidine,3 carbohydrate substituted benzoquinones,4 and of the oxazole segment of calyculin5 have been accomplished using this chiral synthon. |
| Melting point | 67-69 °C(lit.) |
| Protective equipment | Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter |
|---|---|
| Water hazard class (WGK, DE) | 3 |
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 (–)-2,3-O-Isopropylidene-D-erythronolactone used for?
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This compound is a chiral synthon used in organic synthesis, particularly in carbohydrate chemistry. It is employed in Aldol condensations, spiroannulated carbohydrate synthesis, and in the preparation of complex molecules such as indolizidines and segments of natural products like calyculin.
What are the CAS number and formula for (–)-2,3-O-Isopropylidene-D-erythronolactone?
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The CAS number is 25581-41-3, and the empirical formula is C7H10O4.
What grade and purity does Tech Serve Solutions supply for (–)-2,3-O-Isopropylidene-D-erythronolactone?
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Tech Serve Solutions supplies (–)-2,3-O-Isopropylidene-D-erythronolactone with an assay of 98%. We do not represent this product as USP, BP, EP, or other pharmacopoeia grades unless explicitly stated in the product specifications.
What are the safety and handling recommendations for (–)-2,3-O-Isopropylidene-D-erythronolactone?
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Based on available safety data, appropriate personal protective equipment includes eyeshields, gloves, and a type N95 (US) or type P1 (EN143) respirator filter. The compound is classified under WGK 2 in Germany, indicating it is hazardous to water.
How is (–)-2,3-O-Isopropylidene-D-erythronolactone packed, shipped, or exported?
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Tech Serve Solutions adheres to all relevant regulations for the packing, shipping, and exporting of chemicals, ensuring safe and compliant handling of (–)-2,3-O-Isopropylidene-D-erythronolactone for global distribution.
How can I request a sample or quote for (–)-2,3-O-Isopropylidene-D-erythronolactone?
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To request a sample or a quote for (–)-2,3-O-Isopropylidene-D-erythronolactone, please contact our sales team through the website or by calling our customer service number.
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