69504-14-9

Usage

Uses

Used in Chemical Synthesis:
3'-O-tert-Butyldimethylsilyladenosine is used as a protective agent in chemical synthesis for [application reason] the 3'-OH group of adenosine. The TBDMS group shields the hydroxyl group, preventing unwanted reactions and facilitating the synthesis of more complex molecules.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 3'-O-tert-Butyldimethylsilyladenosine is used as a research tool for [application reason] understanding the effects of modifying the 3'-OH group of adenosine on biological activity. This knowledge can contribute to the development of new drugs with improved efficacy and stability.
Used in Biological Research:
3'-O-tert-Butyldimethylsilyladenosine serves as a valuable probe in biological research for [application reason] studying the role of adenosine and its derivatives in cellular processes. 3'-O-tert-Butyldimethylsilyladenosine's altered properties can provide insights into adenosine receptor interactions and signal transduction pathways.

Upstream product

• 69504-03-6 3',5'-bis-O-(tert-butyldimethylsilyl)-β-D-adenosine 
• 1237843-27-4 3'-O-tert-butyldimethylsilyl-5'-O-triethylsilyl-2'-deoxy-adenosine 
• 69504-13-8 2'-O-(tert-butyldimethylsilyl)adenosine 

Downstream Products

• 69504-13-8 2'-O-(tert-butyldimethylsilyl)adenosine 

Relevant academic research and scientific papers

Chemoselective deprotection of triethylsilyl ethers

An efficient and selective method was developed for the deprotection of triethylsilyl (TES) ethers using formic acid in methanol (5-10%) or in methylene chloride 2-5%) with excellent yields. TES ethers are selectively deprotected to the corresponding alco

Ceric ammonium nitrate on silica gel for efficient and selective removal of trityl and silyl groups

Silicna gel-supported ceric ammonium nitrate (CAN-SiO2) was found effective for rapid and selective cleavage of trityl (Tr), monomethoxytrityl (MMTr), and dimethoxytrityl (DMTr) groups from protected nucleosides and nucleotides under mild conditions. Efficiency of deprotections depended upon the stability of th resultant carbocationic species: DMTr+ > MMTr+ > Tr+. Use of a catalytic amount of this solid-supported reagent can also efficiently and selectively remove the tert butyldimethylsilyl or the triisopropylsilyl group from a primary hydroxyl functionality in di- or trisilyl ethers of ribonucleosides. A comparative stud of deprotection reactions by utilization of CAN alone or CAN-SiO2 indicates a remarkable increase in the rate of the reactions involving a solid support. The mechanism of electron-transfer processes is proposed for the use of CAN-SiO2 in the removal of these protective groups from organic molecules.

ISOMERIZATION OF tert-BUTYLDIMETHYLSILYL PROTECTING GROUPS IN RIBONUCLEOSIDES

The tert-butyldimethylsilyl group undergoes isomerization between O-2' and O-3' in ribonucleosides in solution.Isomerization is most rapid in protic solvents and extremely slow in such solvents as dry dimethyl sulfoxide, pyridine, oxolane, chloroform, or