292637-05-9

Basic information

• Product Name: Uridine, 2',3'-O-(1-methylethylidene)-5'-O-[tris(1-methylethyl)silyl]-
• CAS NO: 292637-05-9
• Molecular Formula: C21H36N2O6Si
• Molecular Weight: 440.612
• Mol File: 292637-05-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Uridine, 2',3'-O-(1-methylethylidene)-5'-O-[tris(1-methylethyl)silyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Uridine, 2',3'-O-(1-methylethylidene)-5'-O-[tris(1-methylethyl)silyl]-(292637-05-9)
• EPA Substance Registry System: Uridine, 2',3'-O-(1-methylethylidene)-5'-O-[tris(1-methylethyl)silyl]-(292637-05-9)

Safety Data

• Hazardous Substances Data: 292637-05-9(Hazardous Substances Data)

Upstream product

• 362-43-6 2',3'-O-isopropylideneuridine 
• 80522-42-5 triisopropylsilyl trifluoromethanesulfonate 

Downstream Products

• 801316-83-6 2',3'-O-isopropylidene-5'-O-(triisopropylsilyl)uridine-6-methyl-(6¹->5')-N⁶-benzoyl-2',3'-O-isopropylideneadenosine 
• 801316-79-0 6-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-1-((3aR,4R,6R,6aR)-2,2-dimethyl-6-triisopropylsilanyloxymethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-1H-pyrimidine-2,4-dione 
• 801316-80-3 6-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-1-((3aR,4R,6R,6aR)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-1H-pyrimidine-2,4-dione 
• 582295-71-4 C₆₄H₇₇N₇O₁₄Si 

Relevant articles and documents

Oligonucleosides with a nucleobase-including backbone. Part 1. Concept, force-field calculations, and synthesis of uridine-derived monomers and dimers

A new type of oligonucleosides has been devised to investigate the potential of oligonucleosides with a nucleobase-including backbone to form homo- and/or heteroduplexes (cf. Fig. 2). It is characterised by ethynyl- linkages between C(5') and C(6) of uridine, and between C(5') and C(8) of adenosine. Force-field calculations and Maruzen model studies suggest that such oligonucleosides form autonomous pairing systems and hybridize with RNA. We describe the syntheses of uridine-derived monomers, suitable for the construction of oligomers, and of a dimer. Treatment of uridine-5'- carbaldehyde (2) with triethylsilyl acetylide gave the diastereoisomeric propargylic alcohols 6 and 7 (1:2, 80%; Scheme 1). Their configuration at C(5') was determined on the basis of NOE experiments and X-ray crystal- structure analysis. Iodination at C(6) of the (R)-configured alcohol 7 by treatment with lithium diisopropylamide (LDA) and N-iodosuccinimide (NIS) gave the iodide 17 (62%), which was silylated at O-C(5') to yield 18 (89%; Scheme 2). C-Desilylation of 7 with NaOH in MeOH/H2O led to the alkyne 10 (98%); O-silylation of 10 at O-C(5') gave 16 (84%). Cross-coupling of 18 and 16 yielded 63% of the dimer 19, which was C-desilylated to 20 in 63% yield. Cross-coupling of 10 and the 6-iodouridine 13 (70%), followed by treatment of the resulting dimer 14 with HF and HCl in MeCN/H2O, gave the deprotected dimer 15 (73%).