16640-05-4

Basic information

• Product Name: 1-(β-D-arabinofuranosyl)-N⁴-benzoylcytosine
• Synonyms: 1-(β-D-arabinofuranosyl)-N⁴-benzoylcytosine
• CAS NO: 16640-05-4
• Molecular Weight: 347.327
• Mol File: 16640-05-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1-(β-D-arabinofuranosyl)-N⁴-benzoylcytosine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(β-D-arabinofuranosyl)-N⁴-benzoylcytosine(16640-05-4)
• EPA Substance Registry System: 1-(β-D-arabinofuranosyl)-N⁴-benzoylcytosine(16640-05-4)

Safety Data

• Hazardous Substances Data: 16640-05-4(Hazardous Substances Data)

Upstream product

• 147-94-4 arabinosyl cytosine 
• 69-74-9 cytarabine hydrochloride 
• 51432-43-0 4-Amino-1-((2R,3S,4R,5R)-3,4-bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one 
• 93-97-0 benzoic acid anhydride 

Downstream Products

• 87418-92-6 N-benzoyl-1-(5'-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl)cytidine 
• 81256-87-3 N-{1-[(2R,3S,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide 
• 373645-96-6 N-{1-[(2R,3S,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide 
• 72409-30-4 N-(1-{(2R,3S,4R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-hydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-2-oxo-1,2-dihydro-pyrimidin-4-yl)-benzamide 
• 87418-82-4 N-(1-{(2R,3S,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-2-oxo-1,2-dihydro-pyrimidin-4-yl)-benzamide 
• 608122-28-7 N-benzoyl-1-(2',3'-di-O-acetyl-β-D-arabinofuranosyl-5'-monophosphate-1-dodecylthio-2-decyloxypropyl)cytidine 
• 608122-27-6 N-benzoyl-1-(2',3'-di-O-acetyl-5'-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl)cytidine 
• 332863-97-5 N-benzoyl-1-(2',3'-di-O-acetyl-β-D-arabinofuranosyl)cytidine 
• 87418-75-5 N⁴-benzoyl-5'-O-monomethoxytritylarabinocytidine 
• 87418-76-6 N-(1-{(2R,3S,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3,4-dihydroxy-tetrahydro-furan-2-yl}-2-oxo-1,2-dihydro-pyrimidin-4-yl)-benzamide 
• 82845-93-0 N-{1-[(2R,3S,4R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide 
• 82845-97-4 N⁴-benzoyl-1-[3',5'-bis-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl]cytosine 

Relevant articles and documents

An improved transient method for the synthesis of N-benzoylated nucleosides

The Jones' transient method for the synthesis of N-benzoylated nucleosides is improved by reducing the amounts of chlorotrimethylsilane (TMSCl) and benzoyl chloride to nearly equivalent quantities. The easy work-up and high yields of products are the major advantages of this approach. Jones' method is further simplified by omitting the addition of ammonium hydroxide. The utility of this modification for the preparation of some useful protected nucleosides is also presented.

Selective cleavage of O-(dimethoxytrityl) protecting group with sodium periodate

Sodium periodate in aqueous organic solvents selectively removes, under mild reaction conditions, the O-(dimethoxytrityl) protecting group. Selectivity of the cleavage was studied using the nucleoside derivatives protected by various types of groups commonly used in nucleoside and nucleotide chemistry.