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Description
2,3:4,5-Di-O-isopropylidene-beta-D-fructopyranose is a protected sugar derivative obtained from D-fructose, in which two pairs of hydroxyl groups are locked as isopropylidene acetals. The compound belongs to the field of glycoscience, the applied chemistry of carbohydrates, and serves as a ready-to-use chiral starting material in the laboratory. With four hydroxyl groups already protected, only a single position remains available for modification, allowing researchers to carry out selective reactions on the sugar framework without working through the long and time-consuming sequences of protection and deprotection steps that would otherwise be required.
The property that makes this compound valuable is the inherent chirality of a naturally occurring sugar combined with a neat, clearly defined protection pattern. The fructopyranose framework provides a rigid scaffold with well-ordered stereogenic centres, so derivatives prepared from it can direct reactions toward products with high enantiomeric excess. The isopropylidene acetals are stable under basic and neutral conditions yet can be removed under aqueous acidic conditions, giving the researcher full control over exactly when the hydroxyl groups are released again. This predictable balance of stability and selective removability is what distinguishes it from unprotected sugars.
In Indonesian laboratories, this material is typically used in university and institutional research groups working on carbohydrate chemistry, asymmetric synthesis, and the preparation of chiral building blocks. It is handled as a solid on the analytical or preparative scale, dissolved in a suitable organic solvent, and taken forward through selective transformations at the remaining free position. Because it arrives ready protected, it shortens synthetic routes considerably, which is a practical advantage where reagent lead times and solvent budgets are limited.
Laboratory Applications
- Asymmetric synthesis — the fixed stereogenic centres of the fructopyranose framework can transfer chirality to new bonds, helping reactions deliver products with high enantiomeric excess.
- Chiral building block preparation — a single unprotected position allows the sugar core to be elaborated selectively into more complex chiral intermediates without competing side reactions.
- Glycoscience and carbohydrate chemistry research — it offers a well-defined protected fructose scaffold for studying reactivity, stereochemistry, and selective functionalisation of pyranose ring systems.
- Selective functionalisation studies — because four hydroxyls are already masked as acetals, chemists can probe reactions at one site and interpret results without ambiguity.
- Protecting-group methodology work — the isopropylidene acetals are stable to base and neutral media but cleavable in aqueous acid, making the compound useful for demonstrating and optimising deprotection conditions.
Specifications
- Brand: TCI
- Product code: D3758
- CAS number: 20880-92-6
- Category: Chemistry > Chemical Biology > Glycoscience
- Physical form: solid, soluble in suitable organic solvents
- Pack sizes: available in standard TCI research-scale packaging; please confirm the size options when ordering
- Storage: store in a closed container in a cool, dry place away from moisture and acidic vapours
Handling and Storage
Store the compound in its original tightly closed container in a cool, dry place, protected from moisture and away from acids or acidic vapours, since the isopropylidene acetals are cleaved under aqueous acidic conditions. Amber glass or the supplier's original bottle is suitable, kept sealed to limit exposure to atmospheric humidity. Handle the solid in a well-ventilated area or fume hood, using gloves, safety glasses, and a laboratory coat, and avoid generating dust when weighing. Use clean, dry spatulas and glassware to prevent contamination, allow chilled containers to warm to room temperature before opening to avoid condensation, and consult the manufacturer's safety data sheet before use.
