84500-33-4

Basic information

• Product Name: 5-Iodo-2',3',5'-tri-O-acetyluridine
• Synonyms: 5-Iodo-2',3',5'-tri-O-acetyluridine;2',3',5'-Tri-O-acetyl-5-iodouridine;5-Iodo-1-(2,3,5-tri-O-acetyl-beta-D-arabinofuranosyl)-2,4(1H,3H)-pyrimidinedione
• CAS NO: 84500-33-4
• Molecular Formula: C₁₅H₁₇IN₂O₉
• Molecular Weight: 496.20795
• Mol File: 84500-33-4.mol
• Article Data: 26

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-Iodo-2',3',5'-tri-O-acetyluridine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Iodo-2',3',5'-tri-O-acetyluridine(84500-33-4)
• EPA Substance Registry System: 5-Iodo-2',3',5'-tri-O-acetyluridine(84500-33-4)

Safety Data

• Hazardous Substances Data: 84500-33-4(Hazardous Substances Data)

Upstream product

• 696-07-1 5-iodouracil 
• 13035-61-5 1,2,3,5-tetraacetylribose 
• 65-46-3 CYTIDINE 
• 5040-18-6 4-N-2',3',5'-O-tetraacetylcytidine 
• 38953-72-9 5-iodo-2,4-bis-O-trimethylsilyluracil 
• 1024-99-3 5-iodouridine 
• 108-24-7 acetic anhydride 
• 58-96-8 uridine 
• 4105-38-8 Tri-O-acetyluridine 

Downstream Products

• 69075-42-9 5-ethynyluridine 
• 1428477-12-6 2’-O-tert-butyldimethylsilyl-5-ethinyl uridine 
• 1428477-07-9 2’-O-tert-butyldimethylsilyl-3‘,5‘-O-bis(tert-butyl)silyl-5-ethinyl uridine 
• 1428477-08-0 2’-O-tert-butyldimethylsilyl-3’,5’-O,O-bis[di(2-cyanoethyl)]phosphoryl-5-ethinyl uridine 
• 1428477-09-1 C₁₁H₁₄N₂O₁₂P₂ 
• 139323-52-7 N-trit-U-morpholino 
• 109205-43-8 2-(2,4-dioxo-4,4-dihydropyrimidin-1(2H)-yl)-6-(hydroxymethyl)morpholine 

Relevant articles and documents

Design, synthesis, and biological evaluation of novel C5-modified pyrimidine ribofuranonucleosides as potential antitumor or/and antiviral agents

Background: Nucleoside analogues are well-known antitumor, antiviral, and chemotherapeutic agents. Alterations on both their sugar and the heterocyclic parts may lead to significant changes in the spectrum of their biological activity and the degree of selective toxicity, as well as in their physicochemical properties. Method: C5-arylalkynyl-β-D-ribofuranonucleosides 3-6, 3?-deoxy 12-15, 3?-deoxy-3?-C-methyl-β-D-ribofurananucleosides 18-21 and 2?-deoxy-β-D-ribofuranonucleosides 23-26 of uracil, were synthesized using a one-step Sonogashira reaction under microwave irradiation and subsequent deprotection. Results: All newly synthesized nucleosides were tested for their antitumor or antiviral activity. Moderate cytostatic activity against cervix carcinoma (HeLa), murine leukemia (L1210) and human lymphocyte (CEM) tumor cell lines was displayed by the protected 3?-deoxy derivatives 12b, 12c, 12d, and the 3?-deoxy-3?-methyl 18a, 18b, 18c. The antiviral evaluation revealed appreciable activity against Coxsackie virus B4, Respiratory syncytial virus, Yellow Fever Virus and Human Coronavirus (229E) for the 3?-deoxy compounds 12b, 14, and the 3?-deoxy-3?-methyl 18a, 18c, 18d, accompanied by low cytotoxicity. Conclusion: This report describes the total and facile synthesis of modified furanononucleosides of uracil, with alterations on both the sugar and the heterocyclic portions. Compounds 12b, 14 and 18a,c,d showed noticeable antiviral activity against a series of RNA viruses and merit further biological and structural optimization investigations.

Effective Synthesis of 5-Iodo Derivatives of Pyrimidine Morpholino Nucleosides

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A solid-supported acidic oxazolium perchlorate as an easy-handling catalyst for the synthesis of modified pyrimidine nucleosides via Vorbrüggen-type N-glycosylation

A solid-supported acidic oxazolium perchlorate was investigated as a heterogeneous catalyst in N-glycosylation reactions using silylated modified pyrimidines and an acylated ribose or glucose to afford the corresponding pyrimidine nucleosides. This salt is a nonhygroscopic and stable powder whose activity is comparable to that of 2-methyl-5-phenylbenzoxazolium perchlorate. A reaction with this polymer catalyst can be conducted on a gram scale. Reusability of the solid-supported catalyst was also investigated.