98495-56-8

Basic information

• Product Name: Uridine, 2'-deoxy-3',5'-O-[1,1,3,3-tetrakis(1-methylethyl)-1,3-disiloxanediyl]-
• Synonyms: 3',5'-(tetraisopropyl-disiloxane-1,3-diyl)-2'-deoxyuridine;3',5'-O-(tetraisopropyldisiloxan-1,3-diyl)-2'-deoxyuridine;3',5'-O-[(tetraisopropyl)disiloxane-1,3-diyl]-2'-deoxyuridine;5',3'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-deoxyuridine;1-((2R,3aS,9aR)-5,5,7,7-Tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-1H-pyrimidine-2,4-dione;3',5'-O-(1,1,3,3-Tetraisopropyldisiloxane-1,3-diyl)-2'-deoxyuridine;2'-deoxyuridine-3',5'-(1,1,3,3-tetraisopropyl)disiloxane
• CAS NO: 98495-56-8
• Molecular Formula: C21H38N2O6Si2
• Molecular Weight: 470.714
• Mol File: 98495-56-8.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: Uridine, 2'-deoxy-3',5'-O-[1,1,3,3-tetrakis(1-methylethyl)-1,3-disiloxanediyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Uridine, 2'-deoxy-3',5'-O-[1,1,3,3-tetrakis(1-methylethyl)-1,3-disiloxanediyl]-(98495-56-8)
• EPA Substance Registry System: Uridine, 2'-deoxy-3',5'-O-[1,1,3,3-tetrakis(1-methylethyl)-1,3-disiloxanediyl]-(98495-56-8)

Safety Data

• Hazardous Substances Data: 98495-56-8(Hazardous Substances Data)

Usage

Description

Uridine, 2'-deoxy-3',5'-O-[1,1,3,3-tetrakis(1-methylethyl)-1,3-disiloxanediyl]is a modified nucleoside with a unique disiloxane linker. This modification enhances the stability and reactivity of the molecule, making it a valuable building block in the synthesis of various biologically active compounds.

Uses

Used in Pharmaceutical Industry:
Uridine, 2'-deoxy-3',5'-O-[1,1,3,3-tetrakis(1-methylethyl)-1,3-disiloxanediyl]is used as a reagent for the synthesis of anti-hepatitis B agents. Its unique disiloxane linker provides enhanced stability and reactivity, which is crucial for the development of effective antiviral drugs.

Upstream product

• 58-96-8 uridine 
• 69304-37-6 1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane 
• 69304-38-7 3',5'-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine 
• 18043-71-5 1,1,3,3-tetraisopropyldisiloxane 
• 951-78-0 2'-deoxyuridine 
• 148504-66-9 1-((2R,3R,3aR,9aR)-3-Bromo-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-1H-pyrimidine-2,4-dione 
• 165589-89-9 5',3'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-O-(phenylaminecarbothioate)uridine 
• 76700-78-2 3',5'-O-(tetraisopropyl-disiloxane-1,3-diyl)-2'-O-phenoxythiocarbonyl-uridine 

Downstream Products

• 1414882-33-9 5'-O-dimethoxytrityl-3'-O-[2-(4-nitrophenyl)ethoxy-N,N-diisopropyl]-2'-deoxyribofuranosyl-3-guanyl-N,N-bis[2-(4-nitrophenyl)ethoxycarbonyl]urea phosphoramidite 
• 1414882-32-8 5'-O-dimethoxytrityl-2'-deoxyribofuranosyl-3-guanyl-N,N-bis-[2-(4-nitrophenyl)ethoxycarbonyl]urea 
• 1414882-29-3 2'-deoxyribofuranosyl-3-guanyl-N,N-bis-[2-(4-nitrophenyl)ethoxycarbonyl]urea 
• 1414882-31-7 5',3'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-deoxyribofuranosyl-3-guanyl-N,N-bis-[2-(4-nitrophenyl)-ethoxycarbonyl]urea 
• 98495-67-1 6-phenylhydroxymethyl-2'-deoxyuridine 
• 98495-64-8 6-phenylthio-2'-deoxyuridine 
• 99680-08-7 4-(4-Chloro-phenylsulfanyl)-1-((2R,3aS,9aR)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-1H-pyrimidin-2-one 
• 342630-78-8 5'-O-(4,4'-Dimethoxytrityl)-N⁴-(1-oxyl-2,2,6,6-tetramethyl-4-piperidinyl)-2'-deoxycytidine 
• 370595-48-5 (2E)-3-[3-(5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-4-hydroxytetrahydrofuran-2-yl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl]-N-[6-({[3-(4-nitrophenyl)-1-adamantyl]acetyl}amino)hexyl]acrylamide 
• 370595-50-9 (2E)-3-[3-(5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-4-hydroxytetrahydrofuran-2-yl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl]-N-[6-(9H-carbazol-2-yloxy)hexyl]acrylamide 
• 370595-49-6 (2E)-3-[3-(5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-4-hydroxytetrahydrofuran-2-yl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl]-N-[6-({[5-(dimethylamino)-1-naphthyl]sulfonyl}amino)hexyl]acrylamide 
• 370595-47-4 (+)-5'-O-(4,4'-dimethoxytrityl)-6-[2-(methoxycarbonyl)ethenyl]-2'-deoxyuridine 
• 876171-19-6 N⁴-{2-[1-(tert-butoxycarbonyl)imidazol-4-yl]ethyl}-5'-dimethoxytrityl-6-methyl-2'-deoxycytidine 
• 876171-23-2 5'-dimethoxytrityl-6-methyl-N⁴-[2-(trifluoroacetylamino)ethyl]-2'-deoxycytidine 

Relevant articles and documents

Tris(trimethylsilyl)[2H]silane-triethylborane system producing the highly diastereoselective deuteration (> 99:1) of 2'-bromo-2'-deoxy- and 2'-O-phenoxythiocarbonylribonucleosides at 0°C

Reductive protylation and deuteration reactions using (Me3Si)3SiH- and (Me3Si)3Si2H-Et3B systems were investigated in view of the differences in bond energy and bond length between the Si-H of (Me3Si)3SiH and the Sn-H of Bu3SnH. Higher diastereoselectivity was obtained in comparison with the reactions using the Bu3SnH- and Bu3Sn2H-Et3B systems; the (Me3Si)3SiH system gave remarkable diastereoselectivity of 98.7% at 0°C, whereas the other system required temperatures below -70°C.

Reactivity of nucleosides with a hydroxyl radical in non-aqueous medium

An experiment was conducted to demonstrate the reactivity of nucleosides with a hydroxyl radical (HO) in non-aqueous medium. Five nucleosides and three purine-derived lesions were taken as targets for HO attack. The reactivity with HO radical was determined by laser flash photolysis (LFP) of N-hydroxypyridine-2-thione (NPT) at 355 nm. Following an established kinetic model, the rate constants for the reaction between HO and the modified nucleobases were determined by using naphthalene as a standard. The values obtained for the silylated 2 -deoxyribonucleosides in acetonitrile are of the same order of magnitude and remarkably lower than diffusion control in this solvent, pointing to a similar reactivity pattern. The result confirmed that the reaction of a hydroxyl radical with 2'-deoxyribonucleosides is in general somewhat slower in acetonitrile than in water.

Preparation of deoxynucleosides

Methods for preparing deoxynucleosides from their corresponding ribonucleosides by forming 3-tert-butylphenoxythiocarbonylderivatives of the ribonucleosides and subsequently effecting radical deoxygenation reactions at the carbon atoms to be deoxygenated.