99519-13-8

Basic information

• Product Name: Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(2-oxo-4-p-tolylsulfanyl-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
• Synonyms: Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(2-oxo-4-p-tolylsulfanyl-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
• CAS NO: 99519-13-8
• Molecular Weight: 476.507
• Mol File: 99519-13-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(2-oxo-4-p-tolylsulfanyl-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(2-oxo-4-p-tolylsulfanyl-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester(99519-13-8)
• EPA Substance Registry System: Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(2-oxo-4-p-tolylsulfanyl-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester(99519-13-8)

Safety Data

• Hazardous Substances Data: 99519-13-8(Hazardous Substances Data)

Upstream product

• 58-96-8 uridine 
• 69304-38-7 3',5'-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine 
• 14057-18-2 1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)uracil 
• 3083-77-0 araU 
• 3736-77-4 2,2'-Anhydrouridine 
• 82855-62-7 4-(1,2,4-triazol-1-yl)-1-(2',3',5'-tri-O-acetyl-β-D-arabinofuranosyl)pyrimidine-2(1H)one 
• 106-45-6 para-thiocresol 
• 4105-38-8 Tri-O-acetyluridine 
• 415903-48-9 3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-2'-O-(trimethylsilyl)uridine 
• 111426-24-5 1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-(6-methyl-pyridin-2-yloxy)-1H-pyrimidin-2-one 
• 111426-25-6 1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-(pyridin-3-yloxy)-1H-pyrimidin-2-one 
• 111426-23-4 1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-(2-oxo-2H-pyridin-1-yl)-1H-pyrimidin-2-one 
• 111426-26-7 1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-(pyridin-2-ylsulfanyl)-1H-pyrimidin-2-one 
• 108782-91-8 1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-(6-methyl-pyridin-3-yloxy)-1H-pyrimidin-2-one 

Downstream Products

• 82855-68-3 4-(p-tolylthio)-1-(β-D-arabinofuranosyl)pyrimidin-2(1H)-one 

Relevant articles and documents

Pyridyl groups for protection of the imide functions of uridine and guanosine. Exploration of their displacement reactions for site-specific modifications of uracil and guanine bases.

For the protection of the O-4 function of uridine and the O-6 of guanosine, 2-, 3- and 4-hydroxypyridines, 2-pyridinethiol, 6-methyl-2-hydroxy- and 6-methyl-3-hydroxypyridines have been employed. These substituted pyridines gave pyridyl-N-and/or pyridyl-O-substituted derivatives, depending both upon the position of the hydroxyl and methyl groups in the pyridine ring, at the C-4 and the C-6 of the uracil and guanine residues, respectively. These groups were found to be good leaving groups for nucleophilic substitution reactions by amines, thiolates and oximate. If needed, the rate of these substitution reactions could be conveniently increased by almost 1000-fold by conversion of the pyridyl moiety to its methiodide.

4-(1,2,4-Triazol-1-yl)- and 4-(3-Nitro-1,2,4-triazol-1-yl)-1-(β-D-2,3,5-tri-O-acetylarabinofuranosyl)pyrimidin-2(1H)-ones. Valuable Intermediates in the Synthesis of Derivatives of 1-(β-D-Arabinofuranosyl)cytosine (Ara-C)

Treatment of the acetylated derivative (3b), which was prepared from uridine in 86 percent overall yield, with tri(1H-1,2,4-triazol-1-yl)phosphine oxide gave compound (6a) in high yield, and with 3-nitro-1,2,4-triazole and diphenyl phosphorochloridate it gave compound (6b) in high yield.When the former product (6a) was allowed to react with ammonia, methylamine, dimethylamine, and morpholine at room temperature, and the products further deacetylated if necessary, ara-C (1; R1=R2=H) and its corresponding 4-N-alkyl derivatives (1; R1=H, R2=Me), (1: R1=R2=Me), and 1,R2= -(CH2)2O(CH2)2-> were obtained in very high yields. 4-N-Phenyl-ara-C (1; R1=H, R2=Ph) was obtained in high yield when compound (6a) or (6b) was heated with aniline in pyridine solution and the products then deacetylated.The nitro-compound (6b) was converted into the ara-C derivative (1; R1=H, R2=CH2CO2Me), and the sulphide (7) was obtained following the deacetylation of the products of the reaction between the 1,2,4-triazolyl derivative (6a), toluene-p-thiol, and triethylamine.