69304-38-7

Basic information

• Product Name: 3',5'-O-(1,1,3,3-Tetraisopropyl-1,3-disiloxanediyl)uridine
• Synonyms: 3',5'-O-(1,1,3,3-Tetraisopropyl-1,3-disiloxanediyl)uridine;1-((6aR,8R,9R,9aS)-9-hydroxy-2,2,4,4-tetraisopropyl-6a,8,9,9a-tetrahydro-6H-furo[3,2-f ][1,3,5,2,4]trioxadisilocin-8-yl)pyriMidine-2,4(1H,3H)-dione;3',5'-TIPS-;3',5'-TIPS-Uridine;3,5-TIPS-U
• CAS NO: 69304-38-7
• Molecular Formula: C₂₁H₃₈N₂O₇Si₂
• Molecular Weight: 486.71
• Mol File: 69304-38-7.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 3',5'-O-(1,1,3,3-Tetraisopropyl-1,3-disiloxanediyl)uridine(CAS DataBase Reference)
• NIST Chemistry Reference: 3',5'-O-(1,1,3,3-Tetraisopropyl-1,3-disiloxanediyl)uridine(69304-38-7)
• EPA Substance Registry System: 3',5'-O-(1,1,3,3-Tetraisopropyl-1,3-disiloxanediyl)uridine(69304-38-7)

Safety Data

• Hazardous Substances Data: 69304-38-7(Hazardous Substances Data)

Usage

General Description

3',5'-O-(1,1,3,3-Tetraisopropyl-1,3-disiloxanediyl)uridine is a chemical compound used in biological research. It is a modified form of uridine, a nucleoside found in RNA, and is often used as a building block in the synthesis of modified RNA molecules for studying their function and behavior. The tetraisopropyl-1,3-disiloxanediyl group attached to the 3' and 5' positions of the uridine molecule provides increased stability and resistance to degradation, making it a valuable tool for studying RNA structure and function. Additionally, the chemical modification can also potentially improve the properties of RNA-based therapeutics, such as antisense oligonucleotides and RNA interference, for use in drug development.

Upstream product

• 18043-71-5 1,1,3,3-tetraisopropyldisiloxane 
• 58-96-8 uridine 
• 119694-66-5 4-O-<(2,4,6-triisopropylphenyl)sulfonyl>-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine 

Downstream Products

• 119694-66-5 4-O-<(2,4,6-triisopropylphenyl)sulfonyl>-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine 
• 108782-94-1 4-{(2R,3R,4R,5R)-4-Hydroxy-5-hydroxymethyl-2-[2-oxo-4-(2,4,6-trimethyl-phenoxy)-2H-pyrimidin-1-yl]-tetrahydro-furan-3-yloxy}-4-methoxy-heptanedioic acid dimethyl ester 
• 83167-61-7 Phenoxy-acetic acid (2R,3R,3aR,9aR)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl ester 
• 117901-68-5 N³-[(triphenylmethyl)sulfenyl]-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine 
• 115264-86-3 C₄₆H₆₁N₄O₁₇PSi₂ 
• 86365-02-8 2'-O-(1,3-benzodithiol-2-yl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine 
• 131474-62-9 1-{(2R,3R,3aR,9aR)-3-[1-(2-Fluoro-phenyl)-4-methoxy-piperidin-4-yloxy]-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl}-1H-pyrimidine-2,4-dione 
• 84828-97-7 1-((6aR,8R,9aR)-2,2,4,4-tetraisopropyl-9-oxotetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)pyrimidine-2,4(1H,3H)-dione 
• 173169-13-6 2'-O-<2-(4-nitrophenyl)ethylsulfonyl>-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine 
• 58-96-8 uridine 
• 213548-32-4 2'-O-[1-(2-chlorophenoxy)ethyl]-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine 
• 213548-30-2 2'-O-(1-phenoxyethyl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine 
• 213548-67-5 1-{(2R,3R,3aR,9aR)-5,5,7,7-Tetraisopropyl-3-[1-(2-phenylsulfanyl-ethoxy)-ethoxy]-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl}-1H-pyrimidine-2,4-dione 
• 213548-31-3 2'-O-[1-(4-methoxyphenoxy)ethyl]-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine 

Relevant articles and documents

The PdCl2/R3SiH system for the silylation of nucleosides

Convenient syntheses of TIPDS-Cl2 and TBDMS-Br from the corresponding hydrides were obtained by using catalytic PdCl2 and CCl4 or CH2Br2, respectively. These systems can be successfully applied in tandem procedures for improved silylation of nucleosides.

NUCLEIC ACID RELATED COMPOUNDS. 42. A GENERAL PROCEDURE FOR THE EFFICIENT DEOXYGENATION OF SECONDARY ALCOHOLS. REGIOSPECIFIC AND STEREOSELECTIVE CONVERSION OF RIBONUCLEOSIDES TO 2 prime -DEOXYNUCLEOSIDES.

Treatment of unhindered secondary alcohols with phenoxythiocarbonyl chloride (phenyl chlorothionocarbonate) in pyridine/dichloromethane, or in acetonitrile with 4-dimethylaminopyridine catalysis for hindered alcohols, gave clean conversion to their O-phenoxythiocarbonyl derivatives. Reductive deoxygenation of these phenyl thionocarbonate esters proceeded smoothly, using tri-n-butyltin hydride and a free radical initiator in warm toluene. Overall conversion yields ranged from 57 to 78% for the naturally occurring nucleosides, nucleoside antibiotics, and methyl beta -D-ribofuranoside.