3-(TERT-BUTYLDIMETHYLSILYLOXY)GLUTARIC ANHYDRIDE | CAS 91424-40-7

Product Overview

3-(tert-Butyldimethylsilyloxy)glutaric anhydride (CAS: 91424-40-7) is a silyl-protected glutaric anhydride derivative widely used as an organic building block in pharmaceutical and fine chemical synthesis. It is a white crystalline solid that serves as a versatile diacid precursor in the synthesis of complex pharmaceutical compounds.

This compound is also known as 3-(tert-Butyldimethylsiloxy)glutaric anhydride, 3-TBDMSO glutaric anhydride, and 4-[tert-butyl(dimethyl)silyl]oxyoxane-2,6-dione.

Product Description

3-(tert-Butyldimethylsilyloxy)glutaric anhydride is a white sheet crystalline powder. It features a tert-butyldimethylsilyl (TBDMS) protecting group attached to the oxygen at the 3-position of the glutaric anhydride ring. The anhydride functionality readily undergoes ring-opening reactions with nucleophiles such as alcohols and amines, making it a valuable intermediate in organic synthesis.

The compound is moisture-sensitive and should be handled under dry conditions. It is stable under recommended storage conditions and is typically stored at room temperature in a tightly closed container.

Technical Specifications

Applications

Pharmaceutical Synthesis (Core Application)

This compound is a key organic building block used in the synthesis of more complex pharmaceutical compounds. It is specifically employed for the preparation of the HMG-CoA reductase inhibitor Pitavastatin (P531040), a widely used statin drug for cholesterol management.

The anhydride functionality enables diverse chemical transformations:

• Ring-Opening Reactions: The anhydride ring readily undergoes ring-opening reactions with nucleophiles such as alcohols and amines. For example, it reacts with (S)-2-hydroxy-2-phenyl-acetic acid benzyl ester to form a key intermediate in rosuvastatin side-chain synthesis.

• Amide Formation: It reacts with primary amines, such as (1S)-1-phenylethylamine, to yield amides. This reaction is particularly useful in the synthesis of statins like pitavastatin.

Organic Synthesis & Catalysis

The compound is used in organic synthesis as a versatile diacid precursor. It has been shown to catalyze the synthesis of hydroxycinnamic acids from hydroxylated cinnamic acid derivatives under mild conditions.

DNA & Nucleic Acid Chemistry

The anhydride can be used to synthesize various phosphoramidite and solid-support reagents for introducing modifications into DNA probes. It serves as a versatile building block in the synthesis of new reagents useful in the chemical synthesis of modified DNA probes.

Material Science

The compound has been referenced in patent literature for applications including reinforced polyethylene wood-plastic materials containing carbon nanotubes and carbon nanotube-doped plant fiber type polymer materials.

Key Benefits

• Key intermediate for the synthesis of Pitavastatin and other statin pharmaceuticals

• Versatile building block enabling ring-opening, amidation, and derivatization reactions

• Silyl-protected glutaric anhydride offering selective reactivity

• High purity grades available (95% – 99%)

• Well-characterized compound with established synthetic utility

• Suitable for pharmaceutical research, process development, and scale-up

• Moisture-sensitive but stable under proper storage conditions

Packaging Options

Storage Recommendations:

• Store in a cool, dry, well-ventilated area

• Keep container tightly closed

• Protect from moisture and humidity

• Store under inert atmosphere if possible