tert-butyl(((3aS,4R,6aR)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)methoxy)diphenylsilane | CAS 03-08-5336

CHEMICAL IDENTIFICATION

• NAME: tert-butyl(((3aS,4R,6aR)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)methoxy)diphenylsilane

• CAS REGISTRY NUMBER: 03-08-5336

• MOLECULAR FORMULA: CₓHᵧO₂SiS (structure includes thieno-dioxol ring, diphenylsilane moiety, and tert-butyl protecting group)

• STRUCTURAL CLASS: Silyl ether, protected carbohydrate/thioacetal derivative

This compound is a specialized silyl ether derivative featuring a diphenylsilyl protecting group attached to a substituted tetrahydrothieno-dioxol ring. It is typically used as an intermediate in complex organic synthesis, particularly in carbohydrate and heterocycle chemistry.

COMPOUND OVERVIEW

tert-butyl(((3aS,4R,6aR)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)methoxy)diphenylsilane | CAS 03-08-5336  is a stereochemically defined silyl ether with a fused thieno[3,4-d][1,3]dioxole core. The compound combines:

• A thieno ring (a sulfur-containing heterocycle) contributing ring rigidity and unique electronic character.

• A dioxolane moiety that is often used as a protecting group or chiral auxiliary in carbohydrate synthesis.

• A diphenylsilyl group (tert-butyldiphenylsilyl, TBDPS) known for its robust hydroxyl protection in multi-step synthesis.

This design makes it valuable in situations where protecting group stability and stereochemical integrity are critical.

KEY FEATURES & BENEFITS

• High Stereochemical Purity: The specified (3aS,4R,6aR) configuration ensures consistent outcomes in asymmetric synthesis applications.

• Robust Protecting Group: The tert-butyldiphenylsilyl (TBDPS) group confers high resistance to acidic and basic conditions compared to smaller silyl protecting groups (e.g., TMS or TES), making this material ideal for prolonged synthetic routes.

• Versatile Intermediate: Useful for the protection of primary and secondary hydroxyls when designing complex molecules, including carbohydrate analogs, heterocycles, or natural product derivatives.

• Functional Group Compatibility: The fused heterocycle can provide sites for further modification through well-established organic transformations (oxidation, substitution, cross-coupling).

APPLICATIONS  of  tert-butyl(((3aS,4R,6aR)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)methoxy)diphenylsilane | CAS 03-08-5336

Organic Synthesis & Method Development

This compound is commonly employed as a protected intermediate in the preparation of more complex molecules. The diphenylsilyl protecting group is widely used due to its:

• Stability to a variety of reaction conditions: including strong bases and mild acids.

• Selective deprotection: The TBDPS group can be removed selectively in the presence of other protecting groups using fluoride ions (e.g., TBAF), facilitating orthogonal protection strategies.

Carbohydrate Chemistry

The dioxolane ring system makes this compound relevant in carbohydrate synthesis where:

• Protecting group strategies are essential for controlling reactivity.

• The thieno ring may act as a bioisostere for oxygen in medicinal chemistry efforts.

Pharmaceutical & Medicinal Chemistry

Though not a final API, this intermediate can be used to build heterocyclic scaffolds or glycomimetic structures — both of which are valuable in drug discovery programs targeting enzymes, receptors, or transporters.

Academic Research

Researchers exploring:

• New protecting group strategies.

• Methodology for asymmetric synthesis.

• Heterocycle functionalization.

may find this compound a useful tool in reaction screening and optimization.

PHYSICAL & CHEMICAL PROPERTIES

Note: Analytical data (NMR, HPLC, MS) can be provided upon request.

SAFETY & REGULATORY

As with many specialized organic intermediates:

• This compound is intended for research and development use only and not for human consumption.

• Consult the Safety Data Sheet (SDS) for complete hazard and first-aid information.

• Use standard organic laboratory safety practices: gloves, protective eyewear, lab coat, and engineering controls.

QUALITY ASSURANCE

ResolveMass Laboratories Inc. provides this compound with:

• Batch-specific analytical certification

• Purity assessment by HPLC/NMR

• Optional chiral purity analysis upon request

We adhere to rigorous quality systems to ensure reproducibility and reliability for research applications.

ORDERING INFORMATION

Available in multiple quantities tailored to your research needs:

• Milligram and gram scales

• Custom packaging options

• Purity options upon request (e.g., ≥95 %, ≥98 %)

For pricing, lead times, and availability, visit the product page on resolvemass.ca or contact our technical support team.

TECHNICAL SUPPORT

Our experienced chemists are available to assist with:

• Technical questions

• Application tips

• Custom synthesis solutions

Visit ResolveMass Laboratories Inc. for more information on this compound and related reagents.