69504-13-8

Basic information

• Product Name: 2'-O-t-ButyldiMethylsilyl adenosine
• Synonyms: 2'-O-t-ButyldiMethylsilyl adenosine;2'-O-TBDMS adenosine
• CAS NO: 69504-13-8
• Molecular Formula: C16H27N5O4Si
• Molecular Weight: 381.50218
• Mol File: 69504-13-8.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2'-O-t-ButyldiMethylsilyl adenosine(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-O-t-ButyldiMethylsilyl adenosine(69504-13-8)
• EPA Substance Registry System: 2'-O-t-ButyldiMethylsilyl adenosine(69504-13-8)

Safety Data

• Hazardous Substances Data: 69504-13-8(Hazardous Substances Data)

Upstream product

• 86734-95-4 9-(2,5-di-O-tert-butyldimethylsilyl-β-D-erythro-pentofuran-3-ulosyl)adenosine 
• 65109-11-7 2',5'-bis-O-(tert-butyldimethylsilyl)adenosine 
• 124583-06-8 9-[2-O-(tert-butyldimethylsilyl)-β-D-erythro-pentofuran-3-ulosyl]adenine 
• 69504-14-9 3'-O-(tert-butyldimethylsilyl)adenosine 

Downstream Products

• 69504-14-9 3'-O-(tert-butyldimethylsilyl)adenosine 

Relevant articles and documents

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