144963-49-5

Basic information

• Product Name: C₃₇⁽¹³⁾CH₂₉N₅O₈
• Synonyms: C₃₇⁽¹³⁾CH₂₉N₅O₈
• CAS NO: 144963-49-5
• Molecular Weight: 684.666
• Mol File: 144963-49-5.mol

Chemical Properties

• CAS DataBase Reference: C₃₇⁽¹³⁾CH₂₉N₅O₈(CAS DataBase Reference)
• NIST Chemistry Reference: C₃₇⁽¹³⁾CH₂₉N₅O₈(144963-49-5)
• EPA Substance Registry System: C₃₇⁽¹³⁾CH₂₉N₅O₈(144963-49-5)

Safety Data

• Hazardous Substances Data: 144963-49-5(Hazardous Substances Data)

Upstream product

• 4005-49-6 N-benzoyladenine 
• 380611-23-4 [1-13C]-1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-furanoside 
• 83866-07-3 1-O-methyl-β-D-[1-13C]ribofuranoside 
• 335595-58-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-<1-13C>ribofuranoside 
• 380611-22-3 Methyl <1-(13)C>-D-ribofuranoside 
• 83866-07-3 1-O-methyl-D-[1-13C]ribofuranoside 
• 144963-47-3 Phenylsulfenyl <1-(13)C>-2,3,5-tri-O-benzoyl-β-D-ribofuranoside 
• 18055-47-5 N-Benzoyl-N,9-bis(trimethylsilyl)adenin 

Downstream Products

• 335595-83-0 [1'-13C]-5'-O-dimethoxytrityl-2'-O-tert-butyldimethylsilyl-N⁶-benzoyladenosine 
• 335595-77-2 [1'-13C]-2'-O-tert-butyldimethylsilyl-3',5'-O-(di-tert-butylsilanediyl)-N⁶-benzoyladenosine 
• 335595-71-6 [1'-13C]-3',5'-O-(di-tert-butylsilanediyl)-N⁶-benzoyladenosine 
• 335595-80-7 [1'-13C]-2'-O-tert-butyldimethylsilyl-N⁶-benzoyladenosine 
• 335595-67-0 [1'-13C]-N⁶-benzoyladenosine 
• 144963-60-0 C₄₆⁽¹³⁾CH₅₂N₇O₇P 
• 144963-53-1 C₃₅⁽¹³⁾CH₄₇N₅O₇SSi₂ 
• 144963-56-4 C₁₆⁽¹³⁾CH₁₇N₅O₄ 
• 335595-83-0 C₄₃⁽¹³⁾CH₄₉N₅O₇Si 
• 335595-77-2 D-[1'-13C]-2'-O-tert-butyldimethylsilyl-3',5'-O-di-tert-butylsilanediyl-N⁶-benzoyladenosine 
• 335595-71-6 D-[1'-13C]-3',5'-O-(di-tert-butylsilanediyl)-N⁶-benzoyladenosine 
• 335595-80-7 D-[1'-13C]-2'-O-tert-butyldimethylsilyl-N⁶-benzoyladenosine 
• 335595-67-0 C₁₆⁽¹³⁾CH₁₇N₅O₅ 
• 201996-55-6 [1'-13C]adenosine 

Relevant articles and documents

Synthesis of isotopically labeled D-[1′-13C]ribonucleoside phosphoramidites

The preparation of fully protected labeled diisopropylamino-β-cyanoethyl-[1′-13C]ribonucleoside phosphoramidites with regioisomeric purity is described. We demonstrated in this paper that a regioselective 2′-O-silylation, through a 3′,5′-O-di-tert-butylsilanediyl protection, has been applied for the synthesis of [1′-13C]ribonucleoside phosphoramidite units. This method allowed us to obtain only the desired 2′-O-silyl-3′-O-phosphoramidites avoiding the undesired 3′-O-silyl-2′-O-phosphoramidite nucleosides isolated by standard procedures. This is a suitable procedure to RNA precursors with respect to the isotope-containing precursors.

Efficient synthesis of D-[1′-13c]-ribonucleosides for incorporation into oligo-RNA

Syntheses of the monomer building blocks used for the solid-phase synthesis of specifically 1′-13C-labeled oligoribonucleotides from the D-[1-13C]ribose is presented. Procedure has been used for the selective formation of 2′-O-silylated ribonucleosides. After 5′-O-dimethoxytritylation, the synthesis of D-[1′-13C] ribonucleoside phosphoramidites has been achieved.

Phenylsulfenyl D-Ribofuranosides as Efficient Ribosyl Donors: Application to the Synthesis of -(Deoxy)Nucleosides

Readily available phenylsulfenyl 2,3,5-tri-O-benzoyl-β-D-ribofuranoside glycosylates silylated nucleobases in a fast, high-yielding and stereoselective reaction promoted by trimethylsilyl trifluoromethanesulfonate.The method has been applied to the synthesis of labelled nucleosides further transformed to building blocks ready for oligodeoxynucleotide construction. Key words: anomeric sulfoxides; silylated nucleobases; nucleosides; 2'-deoxynucleosides.

13C-enriched ribonucleosides: Synthesis and application of 13C-1H and 13C-13C spin-coupling constants to assess furanose and N-glycoside bond conformations

Adenosine (1), cytidine (2), guanosine (3), and uridine (4) have been prepared chemically with 13C enrichment (99 atom %) at C1′ and C2′ of the ribose ring. Reliable synthetic protocols have been developed to permit access to millimole quantities of labeled ribonucleosides required for structural studies of stable isotopically labeled oligonucleotides and for in vivo metabolism studies. High-resolution 1H and 13C NMR spectra of the enriched ribonucleosides have been obtained, and 13C-13C and 13C-1H spin-coupling constants have been measured for pathways within the β-D-ribofuranose ring and across the N-glycoside bond. Related couplings were determined in methyl α- and β-D-ribofuranosides (5, 6), and in two conformationally constrained nucleosides, 2,2′-anhydro-(1-β-D-arabinofuranosyl)uracil (7) and 2′,3′-O-isopropylidene-2,5′-O-cyclouridine (8). The latter data were used to construct a crude Karplus curve for the 13C-C-N-13C coupling pathway across the N-glycoside bond in 1-4. 1H-1H, 13C-1H, and 13C-13C coupling data are used to evaluate current models describing the conformational dynamics of 1-4 in aqueous solution.