3816-77-1

Usage

Uses

Used in Pharmaceutical Research and Development:
2',3'-O-Isopropylidene-5-hydroxyMethyl uridine is used as a key intermediate in the synthesis of nucleoside analogs and pharmaceuticals for its enhanced stability and solubility. The presence of the hydroxymethyl group provides a reactive site for further chemical modifications, facilitating the development of novel therapeutic agents.
Used in Antiviral Drug Development:
In the field of antiviral research, 2',3'-O-Isopropylidene-5-hydroxyMethyl uridine is utilized as a starting material for the creation of antiviral agents. Its unique structure allows for the design of compounds that can target and inhibit viral replication, offering potential treatments for various viral infections.
Used in Anticancer Drug Development:
2',3'-O-Isopropylidene-5-hydroxyMethyl uridine also serves as a crucial component in the development of anticancer drugs. Its chemical properties enable the synthesis of nucleoside analogs that can interfere with cancer cell replication and division, providing a means to combat the progression of cancer.
Used in Chemical Derivatization:
The hydroxymethyl moiety in 2',3'-O-Isopropylidene-5-hydroxyMethyl uridine allows for chemical derivatization, making it a versatile compound for the creation of a wide range of nucleoside-based derivatives. This versatility is essential for exploring new chemical entities with potential applications in various industries, including pharmaceuticals, diagnostics, and materials science.

Upstream product

• 149204-06-8 1,2,3,4-tetrahydro-1-(2',3'-O-isopropylidenethymidyl)-quinoline 
• 60170-16-3 2,3-O-isopropylidene-5-ethoxycarbonylpropylaminomethyluridine 
• 58-96-8 uridine 
• 50-00-0 formaldehyd 
• 362-43-6 2',3'-O-isopropylideneuridine 

Downstream Products

• 111476-31-4 2',3'-O-isopropylidene-5-phenylthiomethyluridine 
• 158532-72-0 2',3'-didehydro-2',3'-dideoxy-5-hydroxymethyluridine 
• 69181-26-6 5-carboxymethylaminomethyluridine 
• 72667-55-1 5-methylaminomethyluridine 
• 1476070-57-1 C₂₃H₂₈F₃N₃O₉S 
• 1476070-55-9 C₂₃H₂₈N₄O₁₀ 
• 1476070-69-5 N-[(1-β-D-ribofuranosyl-1H-pyrimidin-5-yl)methyl]-N-trifluoroacetyltaurine 2-(2,4,5-trifluorophenyl)ethyl ester 
• 1476070-67-3 N-[(1-β-D-ribofuranosyl-1H-pyrimidin-5-yl)methyl]-N-trifluoroacetylglycine2-(p-nitrophenyl)ethyl ester 
• 1476070-63-9 2',3'-O-isopropylidene-N-[(1-β-D-ribofuranosyl-1H-pyrimidin-5-yl)methyl]-N-trifluoroacetyltaurine 2-(2,4,5-trifluorophenyl)ethyl ester 
• 1476070-61-7 2',3'-O-isopropylidene-N-[(1-β-D-ribofuranosyl-1H-pyrimidin-5-yl)methyl]-N-trifluoroacetylglycine 2-(p-nitrophenyl)ethyl ester 
• 111476-40-5 Methanesulfonic acid (3aR,4R,6R,6aR)-6-(2,4-dioxo-5-phenylsulfanylmethyl-3,4-dihydro-2H-pyrimidin-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester 
• 111476-32-5 5'-deoxy-5'-iodo-2',3'-O-isopropylidene-5-phenylthiomethyluridine 
• 156214-50-5 N⁴-triisopropylbenzenesulphonyloxy-5'-O-t-butyldimethylsilyl-2',3'-O-isopropylidene-5-t-butyldimethylsilyloxymethylcytidine 
• 156214-51-6 N⁴-triisopropylbenzenesulphonyloxy-5-hydroxymethyl-2',3'-O-isopropylidenecytidine 

Relevant academic research and scientific papers

Alternative synthetic routes to 2′,3′-didehydro-2′,3′-dideoxy-5-hydroxymethyluridine

Alternative syntheses for the nucleoside analogue 2′,3′-didehydro-2′,3′-dideoxy-5-hydroxymethyluridine starting from 5-methyluridine and uridine are described.

Efficient synthesis of 5-hydroxymethyl pyrimidines and their nucleosides using microwave irradiation

Hydroxymethylation of uracil (1), cytosine (3), 5-hydroxymethyl-2′,3′-O-isopropylideneuridine (5), 5′-O-tert-butyldiphenylsilyl-2′,3′-O-isopropylideneuridine (7), 2′,3′-O-isopropylidenecytidine (9) and 2′,3′-O-isopropylidene-5′-O-tritylcytidine (11) was efficiently carried out with paraformaldehyde in alkaline medium under microwave irradiation in very high yield.

Synthesis and antiviral activity of C-5 substituted analogues of d4T bearing methylamino- or methyldiamino-linker arms

A general strategy is reported for the preparation of C-5-methylamino- or methyldiamino-d4t analogues of 'different sizes'. Reactions of the 2',3'- didehydro-2',3'-dideoxy-C-5 hydroxymethyl precursor (7) with either polymethylene diamines (n = 6, 8, 10 and 12) or propargylamine proceed regioselectively via substitution reactions at the C-5 position of uracil. The compounds were evaluated for antiviral activity and cytotoxicity. No significant activity was observed for compounds 9, 11, and 13, but 10 and 12 exhibited a weak activity against HIV-1.

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.

SYNTHESIS OF 6,5'-cyclo-2',5'-DIDEOXYPYRIMIDINE NUCLEOSIDES ( NUCLEOSIDES AND NUCLEOTIDES. LXXII )

6,5'-cyclo-2',5'-dideoxyuridine and 6,5'-cyclo-5'-deoxythymidine, pyrimidine deoxynucleosides fixed in the anti conformation were synthesized.The key intermediate, 3'-O-acetyl-5-chloro-2',5'-dideoxy-5'-iodouridine ( 12 ), prepared from 2'-deoxyuridine, was cyclized by treatment with tributyltin hydride to the 6,5'-cyclo derivative ( 13 ), then dehydrochlorinated to furnish, after de-O-acetylation, 6,5'-cyclo-2',5'dideoxyuridine ( 14 ).For the synthesis of 6,5'-cyclothymidine, 3'-O-acetyl-2',5'-dideoxy-5'-iodo-5-phenylthiomethyluridine ( 22 ) was prepared from 2'-deoxyuridine and this compound was cyclized by treatment with tributyltin hydride to yield, after de-O-acetylation 6,5'-cyclo-5'-deoxythymidine ( 24 ).Keywords - cyclonucleoside; C-cyclouridine; 6,5'-cyclo-2',5'-dideoxyuridine; 6,5'-cyclo-5'deoxythymidine; 5-bromo-6,5'-cyclo-2',5'-dideoxyuridine; radical cyclization; tributyltin hydride; NMR; CD

Process for preparing 2-thiouracil nucleosides

Some new 1-(2- or 3-deoxy-β-D-pentofuranosyl)-2-thiouracils and 1-β-D-pentofuranosyl-2-thio-6-azauracils have been prepared. Further, it has been found that the known nucleoside compound, 1-β-D-ribofuranosyl-2-thiouracil is active against Herpes virus and against L-1210 leukemia in mice. An improved method of preparing corresponding 2-0-methyluracil and 2-0-methyl-6-azauracil intermediates is described. The method preserves the β-configuration of the starting nucleoside.