37085-43-1

Basic information

• Product Name: 2’,3’-O-isopropylidene-5’-O-(p-toluenesulfonyl)-5-methyluridine
• Synonyms: 2’,3’-O-isopropylidene-5’-O-(p-toluenesulfonyl)-5-methyluridine
• CAS NO: 37085-43-1
• Molecular Weight: 452.485
• Mol File: 37085-43-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2’,3’-O-isopropylidene-5’-O-(p-toluenesulfonyl)-5-methyluridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2’,3’-O-isopropylidene-5’-O-(p-toluenesulfonyl)-5-methyluridine(37085-43-1)
• EPA Substance Registry System: 2’,3’-O-isopropylidene-5’-O-(p-toluenesulfonyl)-5-methyluridine(37085-43-1)

Safety Data

• Hazardous Substances Data: 37085-43-1(Hazardous Substances Data)

Upstream product

• 1463-10-1 5-Methyluridine 
• 2073-43-0 2',3'-O,O-isopropylidene-5-methyluridine 
• 98-59-9 p-toluenesulfonyl chloride 
• 161986-79-4 1-((3aR,4R,6R,6aR)-6-Hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-5-(2H-quinolin-1-ylmethyl)-1H-pyrimidine-2,4-dione 
• 149204-06-8 1,2,3,4-tetrahydro-1-(2',3'-O-isopropylidenethymidyl)-quinoline 
• 60170-16-3 2,3-O-isopropylidene-5-ethoxycarbonylpropylaminomethyluridine 
• 3816-77-1 2',3'-O-isopropylidene-5-hydroxymethyl-uridine 

Relevant articles and documents

Tightly linked morpholino-nucleoside chimeras: new, compact cationic oligonucleotide analogues

The polyanionic phosphodiester backbone of nucleic acids contributes to high nuclease sensitivity and low cellular uptake and is therefore a major obstacle to the biological application of native oligonucleotides. Backbone modifications, particularly charge alterations is a proven strategy to provide artificial oligonucleotides with improved properties. Here, we describe the synthesis of a new type of oligonucleotide analogues consisting of a morpholino and a ribo- or deoxyribonucleoside in which the 5′-amino group of the nucleoside unit provides the nitrogen of the morpholine ring. The synthetic protocol is compatible with trityl and dimethoxytrityl protecting groups and azido functionality, and was extended to the synthesis of higher oligomers. The chimeras are positively charged in aqueous medium, due to theN-alkylated tertiary amine structure of the morpholino unit.

Synthesis and structure-activity relationship of uracil nucleotide derivatives towards the identification of human P2Y6 receptor antagonists

P2Y6 receptor (P2Y6-R) is involved in various physiological and pathophysiological events. With a view to set rules for the design of UDP-based reversible P2Y6-R antagonists as potential drugs, we established structure-activity relationship of UDP analogues, bearing modifications at the uracil ring, ribose moiety, and the phosphate chain. For instance, C5-phenyl- or 3-NMe-uridine-5′-α,β-methylene-diphosphonate, 16 and 23, or lack of 2′-OH, in 12-15, resulted in loss of both agonist and antagonist activity toward hP2Y6-R. However, uridylyl phosphosulfate, 19, selectively inhibited hP2Y6-R (IC50 112 μM) versus P2Y2/4-Rs. In summary, we have established a comprehensive SAR for hP2Y6-R ligands towards the development of hP2Y6-R antagonists.

Insight into the chemical mechanism of thymidylate synthase-catalyzed reaction through the evaluation of chemical models: The role of C6 sulfhydryl addition during the reductive elimination step of the reaction

Thymidylate synthase catalyzes the last step of the de novo synthesis of thymidine-5'-monophosphate (TMP), which has long been a target for the development of effective anticancer agents. Model compounds (15, 16, 17) were used to study the effect of C6 nucleophilic addition on the reductive elimination step of the TS-catalyzed reaction. Results suggest that C6 addition facilitates the reductive elimination of the H2folate moiety of the ternary intermediate (3). Therefore, the reaction pathway (pathway (b)) with the participation of C6 sulfhydryl addition during the reductive elimination process is the energetically favored process. Consequently, the elimination of the cysteine sulfhydryl group from the C6 position is the last step of the reaction before the dissociation of the products from the enzyme.