59237-68-2

Basic information

• Product Name: Cytidine, 5-methyl-, 2',3',5'-tribenzoate
• CAS NO: 59237-68-2
• Molecular Formula: C31H27N3O8
• Molecular Weight: 569.571
• Mol File: 59237-68-2.mol

Chemical Properties

• CAS DataBase Reference: Cytidine, 5-methyl-, 2',3',5'-tribenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Cytidine, 5-methyl-, 2',3',5'-tribenzoate(59237-68-2)
• EPA Substance Registry System: Cytidine, 5-methyl-, 2',3',5'-tribenzoate(59237-68-2)

Safety Data

• Hazardous Substances Data: 59237-68-2(Hazardous Substances Data)

Upstream product

• 554-01-8 5-methylcytosin 
• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 
• 3180-76-5 2',3',5'-tri-O-benzoyluridine 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 163496-05-7 C₃₃H₂₇N₅O₈ 
• 115459-50-2 2,3,5-Tri-O-benzoyl-D-ribofuranose 
• 32865-88-6 2'-O,N⁴-bis-trimethylsilyl-5-methylcytosine 

Downstream Products

• 160107-13-1 N-{1-[(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-tetrahydro-furan-2-yl]-5-methyl-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide 
• 160107-17-5 N-(1-{(2R,3R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3,4-dihydroxy-tetrahydro-furan-2-yl}-5-methyl-2-oxo-1,2-dihydro-pyrimidin-4-yl)-benzamide 
• 160107-15-3 N-benzoyl-5-methylcytidine 
• 329897-76-9 4-amino-1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-5-hydroxymethyl-1H-pyrimidin-2-one 
• 329897-75-8 4-amino-1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidin-2-one 
• 329897-77-0 4-Amino-1-[(2R,3R,4S,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidine-5-carbaldehyde 
• 148608-53-1 5-formylcytidine 
• 2140-61-6 5-methylcytidine 

Relevant articles and documents

Facile methods for the synthesis of 5-formylcytidine

5′-O-Protected 5-methylcytidine 3 was oxidized with Na2S2O8 to give a mixture of the corresponding 5-(hydroxymethyl)- and 5-formylcytidine derivatives, 4 and 5. The hydroxymethyl group of 4 was further oxidized to a formyl group by treatment with ceric(IV) ammonium nitrate (CAN). Alternatively, 2′,3′,5′-O-protected 5-(hydroxymethyl)cytidine 10 was directly oxidized with CAN to give the desired 5-formylcytidine derivative 11. After removal of the protecting groups in each intermediate, 5-formylcytidine (6) was obtained in good yield.

Recognition of RNA by tripler formation: Divergent effects of pyrimidine C-5 methylation

In DNA triple helices, methylation at C-5 of thymine or cytosine is reported to have similar stabilizing effects for both bases. Here we show, however, that methylation of the same positions in RNA triplexes has distinctly different effects than in DNA. We have previously described the use of circular triplex-forming RNA oligonucleotides to recognize RNA sequences. Here it is shown that addition of C-5 methyl groups to uracils in these compounds very significantly increases not only affinity but also sequence selectivity in binding a purine-rich RNA target, as measured by thermal denaturation with various target RNAs. Surprisingly, however, addition of C-5 methyl groups to cytosines actually decreases affinity in binding RNA, while the same substitution in DNB is thermally stabilizing. Possible sources of this divergent behavior are discussed. A synthesis of 5-methylcytidine ribonucleoside 2'-O-silyl-3'-O-phosphoramidite is also described.