40733-26-4

Basic information

• Product Name: 3',5'-BIS-O-(T-BUTYLDIMETHYLSILYL)THYMIDINE
• Synonyms: 3',5'-BIS-O-(T-BUTYLDIMETHYLSILYL)THYMIDINE
• CAS NO: 40733-26-4
• Molecular Formula: C₂₂H₄₂N₂O₅Si₂
• Molecular Weight: 470.75
• Mol File: 40733-26-4.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Solubility: Ethyl Acetate
• CAS DataBase Reference: 3',5'-BIS-O-(T-BUTYLDIMETHYLSILYL)THYMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3',5'-BIS-O-(T-BUTYLDIMETHYLSILYL)THYMIDINE(40733-26-4)
• EPA Substance Registry System: 3',5'-BIS-O-(T-BUTYLDIMETHYLSILYL)THYMIDINE(40733-26-4)

Safety Data

• Hazardous Substances Data: 40733-26-4(Hazardous Substances Data)

Usage

Description

3',5'-BIS-O-(T-BUTYLDIMETHYLSILYL)THYMIDINE, also known as 3'',5''-Bis-O-[(1,1-dimethylethyl)dimethylsilyl]thymidine, is an organic compound that serves as an intermediate in the synthesis of N4,5-Dimethyldeoxycytidine (D468100). 3',5'-BIS-O-(T-BUTYLDIMETHYLSILYL)THYMIDINE plays a significant role in the inhibition of cytidine deaminase, an enzyme involved in the conversion of cytidine to uridine.

Uses

Used in Pharmaceutical Industry:
3',5'-BIS-O-(T-BUTYLDIMETHYLSILYL)THYMIDINE is used as an intermediate compound for the synthesis of N4,5-Dimethyldeoxycytidine (D468100), which is a key component in the development of drugs targeting cytidine deaminase inhibition. This inhibition can potentially lead to the development of novel therapeutics for various diseases and conditions.
Used in Research and Development:
In the field of research and development, 3',5'-BIS-O-(T-BUTYLDIMETHYLSILYL)THYMIDINE is utilized as a valuable compound for studying the mechanisms of cytidine deaminase and its role in various biological processes. This understanding can contribute to the advancement of medical knowledge and the creation of innovative treatments.
Used in Drug Synthesis:
3',5'-BIS-O-(T-BUTYLDIMETHYLSILYL)THYMIDINE is used as a crucial building block in the synthesis of N4,5-Dimethyldeoxycytidine (D468100), which has potential applications in the development of new drugs. Its role in the synthesis process highlights its importance in the pharmaceutical industry and the potential for future drug discoveries.

Upstream product

• 40733-28-6 5'-tert-butyldimethylsilyloxy-2'-deoxythymidine 
• 947251-79-8 3',5'-bis-O-(tert-butyldimethylsilyl)-O⁴-[(2,4,6-trimethylphenyl)sulfonyl]thymidine 
• 98546-51-1 (4-thiomethoxyphenyl)boronic acid 
• 98-80-6 phenylboronic acid 
• 13331-27-6 m-nitrobenzene boronic acid 
• 149104-90-5 4-acetylphenylboronic acid 
• 10365-98-7 3-methoxyphenylboronic acid 
• 5720-07-0 4-methoxyphenylboronic acid 

Downstream Products

• 947251-79-8 3',5'-bis-O-(tert-butyldimethylsilyl)-O⁴-[(2,4,6-trimethylphenyl)sulfonyl]thymidine 
• 53172-91-1 (benzyloxy)(tert-butyl)dimethylsilane 
• 65-71-4 thymin 
• 50-89-5 thymidine 
• 947251-95-8 1-[3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyribofuranosyl]-5-methyl-4-(3-nitrophenyl)pyrimidin-2(1H)-one 
• 947251-94-7 1-[3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyribofuranosyl]-4-(4-acetylphenyl)-5-methylpyrimidin-2(1H)-one 
• 947251-93-6 1-[3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyribofuranosyl]-4-(3-methoxyphenyl)-5-methylpyrimidin-2(1H)-one 
• 947251-88-9 1-[3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyribofuranosyl]-4-(4-methoxyphenyl)-5-methylpyrimidin-2(1H)-one 
• 947251-87-8 1-[3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyribofuranosyl]-5-methyl-4-[4-(methylsulfanyl)phenyl]pyrimidin-2(1H)-one 
• 944149-08-0 1-[2'-deoxy-3',5'-bis-O-(tert-butyldimethylsilyl)ribofuranosyl]-4-phenyl-5-methyl-2-(1H)-pyrimidinone 
• 629642-46-2 2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-oxymethyluridine-3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite 
• 629642-44-0 2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxymethyluridine 
• 354581-63-8 3',5'-bis(O-tert-butyldimethylsilyl)-2'-deoxy-5-(2,3,4,6-tetra-O-benzoyl-β-glucopyranosyl)oxymethyluridine 
• 5116-22-3 2'-deoxy-5-(methoxymethyl)uridine 

Relevant articles and documents

Protecting groups transfer: Unusual method of removal of tr and TBDMS groups by transetherification

The triphenylmethyl (Tr) group undergoes a transfer (transetherification or disproportionation) between the molecules of 5'-O-Tr-2'-deoxynucleosides in a process mediated by anhydrous sulfates of Cu+2, Fe+2, or Ni+2 to yield mixtures of 3',5'-bis-O-Tr and 3'-O-Tr products. If phenylmethanol is present in a reaction medium, detritylation results with concomitant formation of phenylmethyl triphenylmethyl ether. The behavior of t-butyldimethylsilyl (TBDMS) group in 5'-O-TBDMS-2'-deoxynucleosides is exactly the same. Such type of transetherifications was not observed before for the O-Tr and O-TBDMS groups. Copyright Taylor & Francis Group, LLC.