tert-butyl(((3aS,4R,6aR)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)methoxy)diphenylsilane | CAS 1320269-77-9

PRODUCT OVERVIEW

tert-butyl(((3aS,4R,6aR)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)methoxy)diphenylsilane | CAS 1320269-77-9 is a highly specialized, stereochemically defined organic intermediate widely used in advanced synthetic chemistry. This compound incorporates a tert-butyldiphenylsilyl (TBDPS) ether protecting group attached to a rigid, chiral tetrahydrothieno-dioxole framework via a methoxy linker. Due to its structural complexity and robust protecting group chemistry, it is particularly valuable in multi-step synthesis workflows where selectivity, stability, and stereochemical integrity are critical.

At ResolveMass Laboratories Inc., this compound is supplied for research and development applications, supporting synthetic chemists working in medicinal chemistry, carbohydrate chemistry, and heterocyclic compound development.

CHEMICAL IDENTITY & STRUCTURAL CHARACTERISTICS

The molecular architecture of this compound combines several important chemical features:

• A tetrahydrothieno[3,4-d][1,3]dioxole core, which introduces both oxygen and sulfur heteroatoms into a constrained bicyclic system

• Multiple defined stereocenters ((3aS,4R,6aR)), ensuring precise three-dimensional orientation essential for downstream stereoselective synthesis

• A methoxy linkage connecting the heterocyclic scaffold to a bulky silyl protecting group

• A tert-butyldiphenylsilyl (TBDPS) moiety, one of the most sterically demanding and chemically robust silyl protecting groups used in organic chemistry

This combination makes the molecule particularly resistant to undesired side reactions while preserving reactivity at non-protected functional sites.

FUNCTIONAL ROLE IN ORGANIC SYNTHESIS

The primary role of tert-butyl(((3aS,4R,6aR)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)methoxy)diphenylsilane is as a protected intermediate. The TBDPS group is widely chosen when long or demanding reaction sequences are required, as it provides excellent resistance to:

• Mild to moderate acidic conditions

• Oxidative and reductive environments

• Nucleophilic reagents commonly used in carbon–carbon bond formation

This stability allows chemists to perform multiple transformations on other parts of the molecule without risking premature deprotection or structural degradation. Compared to smaller silyl protecting groups, TBDPS offers superior selectivity, particularly for primary alcohol protection in complex molecular settings.

APPLICATIONS  of  tert-butyl(((3aS,4R,6aR)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)methoxy)diphenylsilane | CAS 1320269-77-9

This compound is especially relevant in carbohydrate-derived chemistry and nucleoside analogue synthesis, where selective functional group manipulation is essential. The tetrahydrothieno-dioxole motif can serve as a precursor to sulfur-containing bioactive scaffolds, while the protected hydroxyl functionality enables controlled downstream modifications.

Common research applications include:

• Construction of stereochemically complex intermediates for medicinal chemistry programs

• Multi-step synthesis of heterocyclic and carbohydrate-based compounds

• Development of structure–activity relationship (SAR) libraries

• Use as a protected building block in academic and industrial R&D laboratories

Once the desired transformations are complete, the TBDPS group can be selectively removed under controlled conditions to regenerate the free functional group for final derivatization.

PHYSICAL & CHEMICAL PROPERTIES

Due to the presence of the diphenylsilyl group, this compound is highly lipophilic and typically exhibits strong retention on reverse-phase chromatographic systems. The steric bulk of the TBDPS moiety contributes to enhanced chemical stability and predictable reactivity profiles.

Detailed analytical data such as NMR, LC-MS, and purity profiles are provided in the Certificate of Analysis accompanying each batch supplied by ResolveMass Laboratories Inc., ensuring consistency and traceability for research use.

SAFETY INFORMATION

This product is intended for research use only. Standard laboratory safety practices should be followed, including the use of appropriate personal protective equipment such as gloves, safety glasses, and lab coats. Avoid direct contact, inhalation, or ingestion. Refer to the Safety Data Sheet (SDS) provided by ResolveMass Laboratories Inc. for comprehensive handling and hazard information.

SUMMARY

tert-Butyl(((3aS,4R,6aR)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)methoxy)diphenylsilane (CAS 1320269-77-9) is a premium, research-grade synthetic intermediate engineered for demanding organic synthesis applications. Featuring a robust TBDPS protecting group and a stereochemically defined heterocyclic core, it enables precise control in complex, multi-step synthetic routes. ResolveMass Laboratories Inc. is proud to supply this compound to support cutting-edge chemical research and development worldwide.