3816-77-1

Basic information

• Product Name: 2',3'-O-Isopropylidene-5-hydroxyMethyl uridine
• Synonyms: 2',3'-O-Isopropylidene-5-hydroxyMethyl uridine;2',3'-Di-O-isopropylidene-5-hydroxymethyl uridine;5-Hydroxymethyl-2',3'-(di-O-isopropylidene)uridine;5-(Hydroxymethyl)-2',3'-O-(1-methylethylidene)uridine;5-(Hydroxymethyl)-2',3'-O-isopropylideneuridine
• CAS NO: 3816-77-1
• Molecular Formula: C₁₃H₁₈N₂O₇
• Molecular Weight: 314.29122
• Mol File: 3816-77-1.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2',3'-O-Isopropylidene-5-hydroxyMethyl uridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2',3'-O-Isopropylidene-5-hydroxyMethyl uridine(3816-77-1)
• EPA Substance Registry System: 2',3'-O-Isopropylidene-5-hydroxyMethyl uridine(3816-77-1)

Safety Data

• Hazardous Substances Data: 3816-77-1(Hazardous Substances Data)

Usage

General Description

2',3'-O-Isopropylidene-5-hydroxyMethyl uridine is a chemical compound commonly used in the synthesis of nucleoside analogs and pharmaceuticals. It is a modified form of uridine, containing an isopropylidene group at the 2' and 3' positions and a hydroxymethyl group at the 5' position. This modification enhances the stability and solubility of the compound, making it useful for various research and medical applications. Additionally, the presence of hydroxymethyl moiety can serve as a potential reactive site for further chemical derivatization. Overall, 2',3'-O-Isopropylidene-5-hydroxyMethyl uridine is an important building block in nucleoside chemistry and has potential therapeutic applications in the field of antiviral and anticancer drug development.

Upstream product

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

Downstream Products

• 111476-31-4 2',3'-O-isopropylidene-5-phenylthiomethyluridine 
• 30414-00-7 5-(hydroxymethyl)uridine 
• 158532-72-0 2',3'-didehydro-2',3'-dideoxy-5-hydroxymethyluridine 
• 156703-94-5 C₅₁H₆₃N₅O₁₅Si 
• 156703-97-8 C₅₁H₅₂N₅O₁₆PS 
• 156703-95-6 C₆₃H₇₂N₅O₁₆PS₂Si 
• 202533-78-6 C₅₀H₅₀N₅O₁₆PS 
• 202533-77-5 C₅₈H₅₈N₅O₁₇PS₂ 
• 37085-43-1 2’,3’-O-isopropylidene-5’-O-(p-toluenesulfonyl)-5-methyluridine 
• 156703-96-7 C₅₁H₅₄N₅O₁₇PS 
• 156214-51-6 N⁴-triisopropylbenzenesulphonyloxy-5-hydroxymethyl-2',3'-O-isopropylidenecytidine 
• 156214-50-5 N⁴-triisopropylbenzenesulphonyloxy-5'-O-t-butyldimethylsilyl-2',3'-O-isopropylidene-5-t-butyldimethylsilyloxymethylcytidine 
• 111476-32-5 5'-deoxy-5'-iodo-2',3'-O-isopropylidene-5-phenylthiomethyluridine 
• 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 

Relevant articles and documents

Model studies of thymidylate synthetase. Neighboring-group facilitation of electrophilic substitution reactions of uracil furanosides.

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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.

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.

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