183892-55-9

Basic information

• Product Name: 1-[(2R,4S,5S)-5-Benzoyl-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione
• Synonyms: 1-[(2R,4S,5S)-5-Benzoyl-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione
• CAS NO: 183892-55-9
• Molecular Weight: 430.576
• Mol File: 183892-55-9.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 1-[(2R,4S,5S)-5-Benzoyl-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[(2R,4S,5S)-5-Benzoyl-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione(183892-55-9)
• EPA Substance Registry System: 1-[(2R,4S,5S)-5-Benzoyl-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione(183892-55-9)

Safety Data

• Hazardous Substances Data: 183892-55-9(Hazardous Substances Data)

Upstream product

• 215437-42-6 3'-O-(tert-butyldimethylsilyl)thymidine-5'-carboxylic acid 
• 98-80-6 phenylboronic acid 
• 100-58-3 phenylmagnesium bromide 
• 131118-61-1 3'-tert-butyldimethylsilylthymidine 5'-carboxaldehyde 
• 197070-47-6 1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(hydroxy-phenyl-methyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 

Downstream Products

• 183892-57-1 1-((2R,4S,5S)-5-Benzoyl-4-hydroxy-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione 
• 183892-50-4 4'-C-benzoylthymidine 
• 183892-68-4 4'-C-benzoyl-5'-O-(4,4'-dimethoxytrityl)thymidine 

Relevant articles and documents

Direct Access to Unique C-5’-Acyl Modified Nucleosides through Liebeskind–Srogl Cross-Coupling Reaction

The chemical functionalization at C-5’ position of nucleosides has been significantly less studied compared to the C-1’, C-2’ and C-3’ sugar positions in spite of its potential important role for biological activity. We describe here the synthesis of new carbothioate nucleosides which were then engaged in a Liebeskind-Srogl reaction with various boronic acids for the preparation of diversely modified C-5’-acyl nucleosides. Applied to pyrimidine nucleosides in the DNA and RNA series, the reaction showed a broad substrate scope and more than 25 examples were synthesized in good-to-excellent isolated yields. This general and efficient Pd-catalyzed and Cu(I)-mediated cross-coupling represents a convenient method to prepare a diverse set of 5’-modified nucleosides and paves the way for further transformation into a variety of potentially bioactive compounds via the possible conversion of the C-5’-ketone.