(3aR,6S,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one | CAS 1320269-76-8

PRODUCT NAME

(3aR,6S,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one

CAS Number: 1320269-76-8

SYNONYMS & IDENTIFIERS

• (3aR,6S,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one

• Protected dioxolane-furanone intermediate

• Silyl ether functional intermediate

• CAS: 1320269-76-8

CHEMICAL STRUCTURE & FORMULA

• Molecular Formula: C₂₂H₂₈O₅Si

• Molecular Weight: 396.52 g/mol

• Structure Type: Fused bicyclic lactone with a tert-butyldiphenylsilyl (TBDPS) protecting group

This compound features a protected hydroxymethyl group (tert-butyldiphenylsilyl ether) attached to a bicyclic dihydrofuro[3,4-d][1,3]dioxol-4-one core. The configuration at the stereocenters is specified as (3aR,6S,6aR), indicating defined spatial relationships critical for downstream transformations.

KEY FEATURES & BENEFITS

HIGH-PURITY PROTECTED SYNTHETIC INTERMEDIATE

This compound is manufactured to high purity standards suitable for complex organic synthesis, medicinal chemistry, and process research. The TBDPS protecting group offers enhanced stability under a variety of reaction conditions.

STEREOCHEMICAL DEFINITENESS

The defined stereochemistry (3aR,6S,6aR) ensures reliable behavior in stereospecific transformations, a crucial requirement for synthesis of advanced chiral targets.

VERSATILE FUNCTIONALITY

Featuring both a bicyclic lactone system and a masked hydroxymethyl group, this intermediate can serve as a key building block in multistep syntheses — particularly where controlled deprotection and ring-opening sequences are needed.

SUITABLE FOR SCALE-UP

Our quality control and batch testing ensure that this product performs consistently from milligram to multi-gram scale reactions, supporting both discovery chemistry and early process development.

APPLICATIONS  of  (3aR,6S,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one | CAS 1320269-76-8

The compound is ideally positioned for use in a range of synthetic and pharmaceutical research applications:

MEDICINAL CHEMISTRY

• As a chiral intermediate in the construction of heterocyclic frameworks

• For design and optimization of small molecules with biological activity

• In structure-activity relationship (SAR) studies requiring stereodefined intermediates

TOTAL SYNTHESIS

• Useful in complex natural product synthesis where protected hydroxymethyl groups and bicyclic lactone cores are required

• Facilitates sequential functional group manipulations with minimized side reactions

PROTECTING GROUP STRATEGIES

The TBDPS group provides:

• High resistance to basic and mildly acidic conditions

• Selective removal with fluoride sources (e.g., TBAF) when required

• Compatibility with multi-step synthetic workflows

PROCESS RESEARCH & DEVELOPMENT

• Evaluation in scale-up strategies

• Optimization of deprotection and functionalization sequences

• Assessment of reagent compatibility and step-economy

SYNTHETIC UTILITY & REACTIVITY CHARACTERISTICS

TBDPS PROTECTION

The tert-butyldiphenylsilyl (TBDPS) group is chosen for its:

• Exceptional stability relative to other silyl protecting groups (e.g., TMS, TBDMS)

• Resistance to hydrolysis and migration under a broad range of conditions

• Ability to selectively protect primary alcohol functionality

DIHYDROFURO[3,4-D][1,3]DIOXOL-4(3AH)-ONE CORE

This bicyclic system imparts:

• A rigid framework that can influence downstream stereochemistry

• A lactone handle for ring-opening, nucleophilic attack, or reduction

• Opportunities for diversification via functional group interconversion

ANALYTICAL CHARACTERISTICS & QUALITY ASSURANCE

ResolveMass adheres to strict quality protocols, delivering material with:

• Purity: Verified by HPLC and/or NMR analysis

• Identity Confirmation: Assessed via NMR, MS, and, where applicable, IR spectroscopy

• Batch Consistency: Synthetic reproducibility ensures consistent performance

• Documentation: Commercial batches include a Certificate of Analysis (CoA)

Analytical data and CoA are provided upon request to support your documentation and regulatory needs.

WHY CHOOSE RESOLVEMASS LABORATORIES?

• Expertise in specialty intermediates: High-purity materials designed for advanced synthesis

• Reliable supply: Consistent quality backed by rigorous testing

• Responsive support: Technical assistance and documentation tailored to your project

For pricing, lead times, and custom requests, contact our sales team at ResolveMass Laboratories Inc. or submit an inquiry via resolvemass.ca.