664333-54-4

Basic information

• Product Name: 1-[5-O-(4,4'-dimethoxytrityl)-2-O,2-C-propano-β-D-arabinofuranosyl]uracil
• Synonyms: 1-[5-O-(4,4'-dimethoxytrityl)-2-O,2-C-propano-β-D-arabinofuranosyl]uracil
• CAS NO: 664333-54-4
• Molecular Weight: 586.642
• Mol File: 664333-54-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-[5-O-(4,4'-dimethoxytrityl)-2-O,2-C-propano-β-D-arabinofuranosyl]uracil(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[5-O-(4,4'-dimethoxytrityl)-2-O,2-C-propano-β-D-arabinofuranosyl]uracil(664333-54-4)
• EPA Substance Registry System: 1-[5-O-(4,4'-dimethoxytrityl)-2-O,2-C-propano-β-D-arabinofuranosyl]uracil(664333-54-4)

Safety Data

• Hazardous Substances Data: 664333-54-4(Hazardous Substances Data)

Upstream product

• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 664333-53-3 1-(2-O,2-C-propano-β-D-arabinofuranosyl)uracil 
• 664333-51-1 1-[2-C-(3-methanesulfonyloxypropyl)-3,5-di-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl]uracil 
• 664333-50-0 1-[2-C-(3-hydroxypropyl)-3,5-di-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl]uracil 
• 664333-48-6 1-[2-C-allyl-3,5-di-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl]uracil 
• 664333-52-2 1-[2-O,2-C-propano-3,5-di-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl]uracil 
• 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 

Relevant articles and documents

2′-Spiro ribo- and arabinonucleosides: Synthesis, molecular modelling and incorporation into oligodeoxynucleotides

We have synthesized four conformationally restricted bicyclic 2′-spiro nucleosides via 2′-C-allyl nucleosides as key intermediates. The ribo-configured 2′-spironucleosides 9b and 14b were obtained by a convergent strategy starting from 2-ketofuranose 1 whereas the arabino-configured 2′-spironucleosides 21 and 27 were obtained by a linear strategy with a 2′-ketouridine derivative as starting material. The furanose ring of 9b/14b adopts N-type conformations whereas the furanose ring of 21/27 exists as an N?S equilibrium. These compounds snowed no anti-HIV-1 activity or cytotoxicity. Incorporation of the four 2′-spironucleosides (as monomers X4 and X5) into oligodeoxynucleotides was accomplished using the phosphoramidite approach on an automated DNA synthesizer. Irrespective of monomeric configuration, hybridization studies revealed that these 2′-spironucleotide monomers (X4 and X5) induce decreased duplex thermostabilities compared with the corresponding DNA:DNA and DNA:RNA duplexes. Molecular modelling indicated that steric constraints are a possible reason for the lowered binding affinities of the modified oligodeoxynucleotides towards complementary single-stranded DNA and single-stranded RNA complements.