(3aR,6S,6aR)-6-(hydroxymethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one | CAS 152006-17-2

PRODUCT OVERVIEW

(3aR,6S,6aR)-6-(hydroxymethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one | CAS 152006-17-2  is a stereochemically well-defined, carbohydrate-derived bicyclic lactone widely utilized as a high-value synthetic intermediate in advanced organic and medicinal chemistry research. With the molecular formula C₈H₁₂O₅ and a molecular weight of 188.18 g/mol, this compound exhibits a rigid fused-ring architecture that is particularly advantageous for stereoselective transformations.

The molecule contains a dihydrofuran ring fused to a 1,3-dioxolane system, stabilized by two methyl substituents and a reactive lactone functionality. The presence of a primary hydroxymethyl group at the C-6 position further enhances its synthetic versatility, enabling downstream derivatization through oxidation, substitution, or conjugation reactions. The defined absolute configuration (3aR,6S,6aR) makes this compound especially valuable for applications requiring strict stereochemical control.

CHEMICAL INFORMATION

• Chemical Name: (3aR,6S,6aR)-6-(Hydroxymethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one

• CAS Number: 152006-17-2

• Molecular Formula: C₈H₁₂O₅

• Molecular Weight: 188.18 g/mol

• Stereochemistry: Defined chiral centers at 3a, 6, and 6a

• Functional Groups: Lactone, acetal (dioxolane), primary alcohol

• Chemical Class: Carbohydrate-derived bicyclic lactone

This compound typically appears as a white to off-white solid under standard laboratory conditions. Its oxygen-rich framework contributes to both chemical stability and predictable reactivity under controlled synthetic conditions.

STRUCTURAL AND FUNCTIONAL CHARACTERISTICS

The bicyclic framework of this compound imparts conformational rigidity, which is highly desirable in synthetic chemistry when precise molecular orientation is required. The 1,3-dioxolane ring functions as a protecting group motif commonly used in carbohydrate chemistry, while the lactone moiety serves as a chemically activated site for nucleophilic reactions.

The hydroxymethyl substituent provides an accessible handle for further functionalization, allowing chemists to introduce additional groups without disrupting the core scaffold. Together, these features make the molecule an excellent platform intermediate for constructing more complex, functionally rich molecules.

SYNTHETIC ORIGIN AND CHEMISTRY

This compound is typically synthesized from protected monosaccharide precursors through a series of regioselective protection, cyclization, and oxidation steps. Acetonide protection strategies are often employed to control hydroxyl group reactivity, followed by intramolecular cyclization to form the fused bicyclic system.

The controlled synthesis preserves stereochemical integrity throughout the process, ensuring reproducibility and reliability for research applications. Because of its predictable reactivity profile, this compound integrates seamlessly into multistep synthetic workflows, particularly in carbohydrate and natural product chemistry.

APPLICATIONS  of  (3aR,6S,6aR)-6-(hydroxymethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one | CAS 152006-17-2

Carbohydrate and Glycochemistry Research

This compound is widely used as an intermediate in the synthesis of carbohydrate analogues, glycomimetics, and structurally modified sugars. Its protected diol system allows selective deprotection and functional group manipulation, making it a valuable tool for studying carbohydrate structure–function relationships.

Chiral Building Block in Organic Synthesis

With three well-defined stereocenters, the compound serves as an effective chiral synthon for asymmetric synthesis. It is frequently incorporated into reaction sequences where stereochemical precision is critical, such as the development of enzyme inhibitors or complex natural product analogues.

Advanced Synthetic Method Development

The lactone functionality enables ring-opening reactions, reductions, and nucleophilic additions, providing access to a broad range of downstream derivatives. Researchers often use this scaffold to evaluate new synthetic methodologies or optimize reaction conditions involving oxygen-rich heterocycles.

QUALITY AND ANALYTICAL CONSIDERATIONS

At ResolveMass Laboratories Inc., compounds of this class are typically characterized using advanced analytical techniques such as LC–MS, NMR spectroscopy, and high-resolution mass spectrometry to ensure structural integrity, stereochemical purity, and consistency. High chemical purity and batch-to-batch reliability are critical for reproducible research outcomes, particularly in multistep synthesis programs.

SUMMARY

(3aR,6S,6aR)-6-(hydroxymethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one | CAS 152006-17-2  is a robust, stereochemically precise bicyclic lactone that plays a key role in modern synthetic and carbohydrate chemistry. Its structural rigidity, functional versatility, and well-defined chirality make it a highly sought-after intermediate for researchers working in advanced organic synthesis, glycoscience, and complex molecule development.