4336-39-4

Basic information

• Product Name: (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diacetate
• Synonyms: (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diacetate
• CAS NO: 4336-39-4
• Molecular Weight: 384.343
• Mol File: 4336-39-4.mol
• Article Data: 17

Chemical Properties

• CAS DataBase Reference: (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diacetate(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diacetate(4336-39-4)
• EPA Substance Registry System: (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diacetate(4336-39-4)

Safety Data

• Hazardous Substances Data: 4336-39-4(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 127761-87-9 (3R,4R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-2,6-dioxa-bicyclo[3.1.0]hexan-4-ol 
• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 
• 1463-10-1 5-Methyluridine 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 3180-76-5 2',3',5'-tri-O-benzoyluridine 
• 65024-85-3 1-β-D-ribofuranosyl-1H-benzotriazole 
• 1311109-67-7 2,3,5-tri-O-acetyl-β-D-ribofuranosyl ortho-hexynylbenzoate 
• 65-71-4 thymin 
• 13035-61-5 1,2,3,5-tetraacetylribose 
• 817197-67-4 (2R,5S)-2-(acetoxymethyl)-5-(p-tolylthio)tetrahydrofuran-3,4-diyl diacetate 
• 40554-98-1 [(2R,3R,4R)-3,4-diacetoxy-5-chlorotetrahydrofuran-2-yl]methyl acetate 
• 28708-32-9 1,2,3,5-tetra-O-acetyl-D-ribofuranose 
• 1314639-86-5 di-tert-butylisobutylsilyl trifluoromethanesulfonate 

Downstream Products

• 1463-10-1 5-Methyluridine 
• 143485-05-6 7'-O-(4,4'-dimethoxytrityl)-5-methylmorpholino uridine 
• 1037305-43-3 6'-O-(4,4'-dimethoxytrityl)-3'-O-cyanoethyl-1'-(N¹-thymidine) morpholino (N,N-diisopropylamino) phosphorodiamidite 
• 138239-62-0 1-((2R,3R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3,4-dihydroxytetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione 
• 3056-17-5 stavudin 
• 173169-45-4 O⁴-2-<4-(cyanophenyl)ethyl>-5'-O-(monomethoxytrityl)ribosylthymine 
• 173170-13-3 2',3',5'-tri-O-acetyl-O⁴-2-<(4-cyanophenyl)ethyl>ribosylthymine 
• 173169-10-3 O⁴-2-<(4-nitrophenyl)ethyl>ribosylthymine 
• 173169-09-0 O⁴-2-<(4-cyanophenyl)ethyl>ribosylthymine 
• 173169-08-9 2',3',5'-tri-O-acetyl-O⁴-(triisopropylbenzenesulfonyl)ribosylthymine 

Relevant articles and documents

Transglycosylation in the Modification and Isotope Labeling of Pyrimidine Nucleosides

Transglycosylation of pyrimidine nucleosides is demonstrated in a one-pot synthesis of uridine derivatives under microwave irradiation. Inductive activation of 2′,3′,5′-tri-O-acetyl uridine with a 5-nitro group produces a more-reactive glycosyl donor. Under optimized Vorbrüggen conditions, the 5-nitrouridine facilitates a reversible nucleobase exchange with a series of 5-substituted uracils. The protocol is also exemplified in a gram-scale reaction under thermal heating. The strategy provides easy access to isotopically labeled uridine.

Cyano Modification on Uridine Decreases Base-Pairing Stability and Specificity through Neighboring Disruption in RNA Duplex

5-Cyanomethyluridine (cnm5U) and 5-cyanouridine (cn5U), the two uridine analogues, were synthesized and incorporated into RNA oligonucleotides. Base-pairing stability and specificity studies in RNA duplexes indicated that cnm5/

Larger laboratory scale synthesis of 5-methyluridine and formal synthesis of its L-enantiomer

A larger laboratory scale synthesis (>60 g per run) of 5-methyluridine is presented. The critical intermediate 1,2-O-isopropylidene-α-D-ribofuranose was prepared from very cheap D-glucose via D-allose. Its L-enantiomer was obtained from L-arabinose via L-glucose, and also from L-xylose. {figure presented}.