13491-47-9

Basic information

• Product Name: 4-(acetylamino)-1-pentofuranosylpyrimidin-2(1H)-one
• Synonyms: 2(1H)-pyrimidinone, 4-(acetylamino)-1-pentofuranosyl-; 4-Acetamido-1-pentofuranosylpyrimidin-2(1H)-one; N1-{1-[3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-2-oxo-1,2-dihydropyrimidin-4-yl}acetamide
• CAS NO: 13491-47-9
• Molecular Formula: C₁₁H₁₅N₃O₆
• Molecular Weight: 285.2533
• Mol File: 13491-47-9.mol
• Article Data: 6

Chemical Properties

• Density: 1.72g/cm³
• Refractive Index: 1.698
• CAS DataBase Reference: 4-(acetylamino)-1-pentofuranosylpyrimidin-2(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(acetylamino)-1-pentofuranosylpyrimidin-2(1H)-one(13491-47-9)
• EPA Substance Registry System: 4-(acetylamino)-1-pentofuranosylpyrimidin-2(1H)-one(13491-47-9)

Safety Data

• Hazardous Substances Data: 13491-47-9(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 147-94-4 arabinosyl cytosine 
• 15890-77-4 acetyl ethyl carbonate 

Downstream Products

• 401812-87-1 N-{1-[(2R,3R,4S,5R)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-acetamide 
• 401812-88-2 N-{1-[(2R,3R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-hydroxy-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-acetamide 
• 15465-98-2 N⁴-acetyl-1-<2',3'-di-O-acetyl-β-D-arabinofuranosyl>cytosine 
• 1245819-13-9 2'-O-(2,4-dinitrophenyl)-3',5'-O-di-tert-butylsilyl-N⁴-acetylarabinocytidine 
• 1245819-15-1 2'-O-(2,4-dinitrophenyl)-N⁴-acetylarabinocytidine 
• 1245819-21-9 5'-O-dimethoxytrityl-2'-O-(2,4-dinitrophenyl)-N⁴-acetylarabinocytidine 

Relevant articles and documents

In-vitro transdermal penetration of cytarabine and its N4-alkylamide derivatives

Objectives: The aim of this study was to synthesise and determine the transdermal penetration of cytarabine alkylamide derivatives and assess the correlation of flux with physicochemical properties. Methods: The alkylamide derivatives of cytarabine were synthesised by acylation at the N4-amino group by the mixed anhydride method. The in-vitro permeation studies were performed using the Franz diffusion cell methodology. Furthermore, partition coefficients (n-octanol-water) and aqueous solubility of the N4-alkylamide derivatives of cytarabine were determined in order to obtain information about their lipophilicity and hydrophilicity. Key findings: The N4-alkylamides of cytarabine (acetyl, butanoyl, hexanoyl, octanoyl, and decanoyl derivatives) showed decreased hydrophilicity and increased lipophilicity. The log D values of the alkylamides were higher than that of the parent compound and increased linearly as the alkyl chain lengthened. N4-hexanoyl-4-amino-1-[(2R,3S,4R,5R)-3,4- dihydroxy-5-(hydroxymethyl)oxolan-2-yl] pyrimidin-2-one) showed the highest median steady-state flux (Jss) of 89.0 nmol/cm2 per h in the series, which shows a high statistical difference with the parent compound flux value (3.70 nmol/cm2 per h). Conclusions The prodrug approach appears to be a promising strategy for the enhancement of transdermal penetration of cytarabine.

Methods for synthesizing nucleosides, nucleoside derivatives and non-nucleoside derivatives

The present invention provides methods for the chemical synthesis of nucleosides and derivatives thereof, including 2′-amino, 2′-N-phthaloyl, 2′-O-methyl, 2′-O-silyl, 2′OH nucleosides, C-nucleosides, nucleoside phosphoramidites, C-nucleoside phosphoramidites, and non-nucleoside derivatives.

Differential reactivity of carbohydrate hydroxyls in glycosylations. II. The likely role of intramolecular hydrogen bonding on glycosylation reactions. Galactosylation of nucleoside 5'-hydroxyls for the syntheses of novel potential anticancer agents

Contrary to expectations, many primary hydroxy groups are completely unreactive in glycosylation reactions, or give the desired glycosides in very low yields accompanied by products of many side reactions. Hydrogens of such primary hydroxyls are shown to be intramolecularly hydrogen bonded. Intermediates formed by nucleophilic attack by these hydroxyls on activated glycosylating agents may resist hydrogen abstraction. This resistance to proton loss is postulated to be the origin of the observed unreactivity. It is shown that successful glycosylations take place under acidic conditions under which such hydrogen bonds cease to exist. Accordingly, direct galactosylations of the normally unreactive 5'-hydroxyls of nucleosides were accomplished for the first time with a galactose trichloroacetimidate donor in chloroform under silver triflate promotion. It is noted that such galactosylated anticancer nucleosides may have improved biological specificity. Contrary to expectations, many primary hydroxy groups are completely unreactive in glycosylation reactions, or give the desired glycosides in very low yields accompanied by products of many side reactions. Hydrogens of such primary hydroxyls are shown to be intramolecularly hydrogen bonded. Intermediates formed by nucleophilic attack by these hydroxyls on activated glycosylating agents may resist hydrogen abstraction. This resistance to proton loss is postulated to be the origin of the observed unreactivity. It is shown that successful glycosylations take place under acidic conditions under which such hydrogen bonds cease to exist. Accordingly, direct galactosylations of the normally unreactive 5′-hydroxyls of nucleosides were accomplished for the first time with a galactose trichloroacetimidate donor in chloroform under silver triflate promotion. It is noted that such galactosylated anticancer nucleosides may have improved biological specificity.