(3aS,4R,6aR)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxole 5-oxide | CAS 2410087-70-4

PRODUCT OVERVIEW

(3aS,4R,6aR)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxole 5-oxide | CAS 2410087-70-4  is a highly specialized, chiral sulfur-containing heterocyclic compound developed for advanced research applications in medicinal chemistry, organic synthesis, and asymmetric methodology development. Its unique combination of a protected hydroxymethyl functionality and a bicyclic thieno[3,4-d][1,3]dioxole core with a sulfoxide group provides a versatile scaffold for chemical transformation and derivatization. This compound is often used as a synthetic intermediate in the construction of complex bioactive molecules, particularly those requiring stringent stereochemical control and functional group compatibility.

CHEMICAL IDENTITY

• IUPAC Name: (3aS,4R,6aR)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxole 5-oxide

• CAS Registry Number: 2410087-70-4

• Molecular Formula: C25H30O4SSi

• Molecular Weight: 444.66 g/mol (approx.)

• Structure Class: Bicyclic heterocycle with sulfoxide and silyl protecting group

STRUCTURAL FEATURES

This compound features a fused bicyclic system consisting of a tetrahydrothieno[3,4-d][1,3]dioxole ring. The presence of the sulfoxide (S=O) moiety at the 5-position adds both polarity and potential for stereochemical influence in downstream reactions. The 4-position bears a tert-butyldiphenylsilyl (TBDPS) ether, providing robust protection for the primary alcohol while imparting steric bulk that can be leveraged in selective transformations. The bicyclic core includes two geminal methyl groups at the 2-position, increasing rigidity and influencing conformational preferences.

The stereochemistry of the compound—specified as (3aS,4R,6aR)—is critical for its utility in asymmetric synthesis and chiral auxiliary strategies. These defined stereocenters enable predictable outcomes in reactions that transfer or transform chirality.

SYNTHETIC UTILITY

The versatile reactivity profile of this compound makes it a powerful building block in multi-step organic syntheses:

• Chiral Sulfoxide Chemistry: Sulfoxides are known to participate in stereoselective transformations, including Pummerer rearrangements and asymmetric oxidations. The sulfoxide group in this scaffold can serve as a directing and activating functionality for controlled functionalization.

• Protected Hydroxymethyl Unit: The TBDPS-protected alcohol can withstand a broad range of reaction conditions, including strong bases and many organometallic reagents. Deprotection under standard fluoride-mediated conditions (e.g., TBAF) reveals a free alcohol for further derivatization.

• Heterocyclic Core Functionalization: The bicyclic thieno[3,4-d][1,3]dioxole ring allows for regioselective C-H functionalizations or ring opening/expansion strategies depending on the targeted synthetic route.

This compound is especially valuable when constructing complex targets in natural product synthesis, analog libraries in drug discovery, and bespoke ligands for catalysis.

APPLICATIONS  of  (3aS,4R,6aR)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxole 5-oxide | CAS 2410087-70-4

Medicinal Chemistry

The structural complexity and tunable functional groups make this intermediate relevant in medicinal chemistry programs focusing on:

• Development of sulfur-containing pharmaceuticals

• Exploration of bioisosteric replacements for oxygen heterocycles

• Synthesis of stereochemically rich candidate molecules for biological screening

Asymmetric Synthesis

• Chiral sulfoxides serve as auxiliaries and catalysts in enantioselective processes.

• The defined stereocenters in this scaffold can be leveraged to induce asymmetry in key bond-forming steps.

Methodology Development

Researchers employing innovative synthetic methodologies—such as C–H activation, photoredox transformations, and metal-catalyzed couplings—can integrate this compound as a structurally unique substrate or intermediate.

ANALYTICAL CHARACTERIZATION

ResolveMass Laboratories Inc. provides comprehensive analytical data to ensure reliability and reproducibility:

• Purity: Typically >95% (by HPLC or GC)

• Chiral Purity: Verified using chiral chromatography techniques

• Structural Confirmation: Confirmed by NMR (1H, 13C), LC-MS, and, where applicable, HRMS

• Melting Point: Provided when solid, to define physical identity

Detailed analytical dossiers are available upon request to support regulatory compliance and publication requirements.

SAFETY INFORMATION

This compound is intended for research use only and must be handled by trained personnel. Safety considerations include:

• Use of appropriate personal protective equipment (PPE): gloves, eye protection, lab coat

• Avoid inhalation, ingestion, or prolonged skin contact

• Consult the Safety Data Sheet (SDS) for hazard classifications, first-aid measures, and disposal protocols

ResolveMass Laboratories Inc. supplies all necessary safety documentation with each shipment.