14057-18-2

Basic information

• Product Name: 1-(2-O,3-O,5-O-Triacetyl-β-D-arabinofuranosyl)-2,4(1H,3H)-pyrimidinedione
• Synonyms: 1-(2-O,3-O,5-O-Triacetyl-β-D-arabinofuranosyl)-2,4(1H,3H)-pyrimidinedione;Spongouridine 2',3',5'-triacetate
• CAS NO: 14057-18-2
• Molecular Formula: C₁₅H₁₈N₂O₉
• Molecular Weight: 370.31142
• Mol File: 14057-18-2.mol
• Article Data: 14

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.43g/cm³
• CAS DataBase Reference: 1-(2-O,3-O,5-O-Triacetyl-β-D-arabinofuranosyl)-2,4(1H,3H)-pyrimidinedione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-O,3-O,5-O-Triacetyl-β-D-arabinofuranosyl)-2,4(1H,3H)-pyrimidinedione(14057-18-2)
• EPA Substance Registry System: 1-(2-O,3-O,5-O-Triacetyl-β-D-arabinofuranosyl)-2,4(1H,3H)-pyrimidinedione(14057-18-2)

Safety Data

• Hazardous Substances Data: 14057-18-2(Hazardous Substances Data)

Usage

Chemical structure

A complex structure that includes a β-D-arabinofuranosyl group and a pyrimidinedione moiety.

Triacetyl groups

Attached to the arabinofuranosyl group, providing protection to the molecule.

Suitability

Suitable for use in chemical reactions and biological studies due to the protective triacetyl groups.

Applications

Potential applications in pharmaceutical research as a drug candidate or a precursor to other bioactive molecules.

Unique structure

Valuable for studying the reactivity and functionalization of sugar-containing molecules in synthetic chemistry.

Protection

The triacetyl groups protect the molecule, allowing for selective reactions and functionalization.

Synthetic utility

The compound can be used as a building block for the synthesis of more complex molecules with potential biological activities.

Biological relevance

The β-D-arabinofuranosyl group is a common structural element in many naturally occurring sugars and glycoconjugates, making this compound relevant for studying carbohydrate-based interactions.

Stability

The triacetyl protection enhances the stability of the molecule, allowing for easier handling and storage.

Potential modifications

The triacetyl groups can be selectively removed or modified to generate new derivatives with different properties and applications.

Upstream product

• 108-24-7 acetic anhydride 
• 2466-76-4 N-Acetylimidazole 
• 3083-77-0 araU 
• 87875-12-5 Acetic acid (2R,3R,4S,5R)-4-acetoxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-3-yl ester 
• 3736-77-4 2,2'-Anhydrouridine 
• 122591-39-3 C₄₅H₄₆N₅O₁₆P 
• 58-96-8 uridine 
• 292037-79-7 O²,2'-anhydro-1-(β-D-arabinofuranosyl)uracil 
• 87418-73-3 5'-O-monomethoxytritylarabinouridine 
• 21016-88-6 2',3'-di-O-acetyl-1-β-D-arabinofuranosyluracil 

Downstream Products

• 21016-88-6 2',3'-di-O-acetyl-1-β-D-arabinofuranosyluracil 
• 3083-77-0 araU 

Relevant articles and documents

Enzymatic regioselective and complete deacetylation of two arabinonucleosides

Candida antarctica lipase B (CAL-B)-catalysed regioselective deacetylation of 2′,3′,5′-tri- O-acetyl-1-β- d-arabinofuranosyluracil (1) and 2′,3′,5′-tri- O-acetyl-9-β- d-arabinofuranosyladenine (2) was studied. The choice of the reaction medium allowed the regioselective formation of products bearing different degree of acetylation: in isopropanol, CAL-B catalysed the formation of the corresponding 2′- O-acetylated arabinonucleosides, while hydrolyses afforded the 2′,3′-di- O-acetylated products. In particular, the procedure herein described allows a simple and efficient preparation of the reported vidarabine prodrug 2′,3′-di- O-acetyl-9-β- d-arabinofuranosyladenine, avoiding the utilisation of protective groups. Moreover, to achieve full deacetylation of the assayed substrates, a set of commercial hydrolases and fungal keratinases from Doratomyces microsporus (DMK) and Paecilomyces marquandii (PMK) were tested. While only PMK and DMK catalysed the quantitative complete deacetylation of 1, DMK accomplished full deacetylation of 2 in shorter time than the other assayed enzymes.

Nucleic Acid Related Compounds. 65. New Syntheses of 1-(β-D-Arabinofuranosyl)-5(E)-(2-iodovinyl)uracil (IVAraU) from Vinylsilane Precursors. Radioiodine Uptake as a Marker for Thymidine Kinase Positive Herpes Viral Infections

(Trimethylsilyl)acetylene was coupled with 1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)-5-iodouracil (3) to give 1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)-5-uracil (4).Lindlar hydrogenation of 4 gave 1-(2,3,4-tri-O-acetyl-β-D-arabinofuranosyl)-5(Z)-uracil (5).Treatment of 5 with iodine monochloride (or sodium iodide/phenyliodine(III) dichloride) in benzene gave 1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)-5(E)-(2-iodovinyl)uracil (7), whereas polar solvents favored the (Z)-iodovinyl isomer 8.Deacetylation of 7gave 1-β-D-arabinofuranosyl)-5(E)-(2-iodovinyl)uracil (IVAraU,9).A microscale in situ synthesis with Na*I gave IVAraU.Treatment of HSV-infected cells with IVAraU resulted in virus-dependent uptake associated with nucleoside phosphorylation by wild type or acyclovir-resistant DNA polymerase mutants (but not with TK-HSV-1 mutants).Uptake was virus-inoculum dependent and was detectable within 4 h postinfection.The process was not completely reversible.Virus-specified uptake of IVAraU may allow automated in vitro detection of HSV isolates.

Selective Acylation of Nucleosides, Nucleotides, and Glycerol-3-phosphocholine in Water

A convenient selective synthesis of 2′,3′-di-O-acetyl-nucleotide-5′-phosphates, 2′,3′-di-O-acetyl-nucleotide-5′-triphosphates and 2′,3′,5′-tri-O-acetyl-nucleosides in water has been developed. Furthermore, a long-chain selective glycerol-3-phosphocholine diacylation is elucidated. These reactions are environmentally benign, rapid, high yielding, and the products are readily purified. Importantly, this reaction may indicate a prebiotically plausible reaction pathway for the selective acylation of key metabolites to facilitate their incorporation into protometabolism.

N4-[Alkyl-(hydroxyphosphono)phosphonate]-cytidine - New drugs covalently linking antimetabolites (5-FdU, araU or AZT) with bone-targeting bisphosphonates (alendronate or pamidronate)

Amino-bisphosphonates (alendronate, pamidronate) were covalently linked in a three step synthesis, with protected and triazolylated derivatives of therapeutically used nucleoside analogs (5-FdU, araC, AZT) by substitution of their triazolyl residue. From the deprotected and chromatographically purified reaction mixtures N4-[alkyl-(hydroxyphosphono) phosphonate]-cytidine combining two differently cytotoxic functions were obtained. This new family of bisphosphonates (BPs) contains as novelty an alkyl side chain with a cytotoxic nucleoside. The BPs moiety allows for a high binding to hydroxyapatite which is a prerequisite for bone targeting of the drugs. In vitro binding of 5-FdU-alendronate (5-FdU-ale) to hydroxyapatite showed a sixfold increased binding of these BPs as compared to 5-FdU. Exploratory cytotoxic properties of 5-FdU-ale were tested on a panel of human tumor cell lines resulting in growth inhibition ranging between 5% and 38%. The determination of IC 50-concentrations of the conjugate in Lewis lung carcinoma and murine macrophages showed an incubation time dependent growth inhibition with higher sensitivity towards the tumor cells. We assume that the antimetabolite-BPs can be cleaved into different active metabolites that may exert cytotoxic and other therapeutic effects. However, the underlying mechanisms of these promising new antimetabolite-BPs conjugates remain to be evaluated in future experiments.