1352789-47-9

Basic information

• Product Name: (3R,S)-1-[3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-1,2-dideoxy-β-D-ribofuranos-1-yl]-5-phenylpent-4-yn-3-ol
• Synonyms: (3R,S)-1-[3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-1,2-dideoxy-β-D-ribofuranos-1-yl]-5-phenylpent-4-yn-3-ol
• CAS NO: 1352789-47-9
• Molecular Weight: 518.841
• Mol File: 1352789-47-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (3R,S)-1-[3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-1,2-dideoxy-β-D-ribofuranos-1-yl]-5-phenylpent-4-yn-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,S)-1-[3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-1,2-dideoxy-β-D-ribofuranos-1-yl]-5-phenylpent-4-yn-3-ol(1352789-47-9)
• EPA Substance Registry System: (3R,S)-1-[3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-1,2-dideoxy-β-D-ribofuranos-1-yl]-5-phenylpent-4-yn-3-ol(1352789-47-9)

Safety Data

• Hazardous Substances Data: 1352789-47-9(Hazardous Substances Data)

Upstream product

• 83540-89-0 3-(β-D-ribofuranosyl)prop-1-ene 
• 69304-37-6 1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane 
• 62410-12-2 1,5-di-O-acetyl-2,3-O-isopropylidene-β-D-ribofuranose 
• 1352789-37-7 3-[3,5-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-1,2-dideoxy-β-D-ribofuranos-1-yl]propanal 
• 4440-01-1 lithium phenylacetylide 
• 1174314-89-6 3-[2-deoxy-3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl]prop-1-ene 
• 1174314-87-4 3-[3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl]prop-1-ene 

Downstream Products

• 1352789-49-1 (3R,S)-1-[3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-1,2-dideoxy-β-D-ribofuranos-1-yl]-5-phenylpent-4-yn-3-one 
• 1373425-74-1 4-[2-[3,5-O-(tetraisopropyldisiloxan-1,3-diyl)-1,2-dideoxy-β-D-ribofuranos-1-yl]ethyl]-2-methyl-6-phenylpyrimidine 

Relevant articles and documents

Synthesis of Homo-C-Nucleoside Phosphoramidites and Their Site-Specific Incorporation into Oligonucleotides

An efficient procedure was developed to prepare homo-C-nucleosides. The β-allyl C-glycoside of D-ribose was transformed into the thienopyrimidine nucleoside and the benzodiazepine nucleoside of 2-deoxy-D-ribose. For incorporation into oligonucleotides by solid-phase synthesis, both derivatives were transformed into the related 3′-phosphoramidite building blocks. These phosphoramidites were then site-specifically incorporated into DNA oligonucleotides. The modified DNA strands were hybridized with different DNA and RNA strands, and their melting temperatures and circular dichroism spectra were studied. Interestingly, although in the case of DNA-DNA hybrids the nonnatural nucleosides caused a marked decrease in melting temperature, to levels even lower than those for mismatched hybrids, in the case of DNA-RNA hybrids very similar melting temperatures were measured for the nonnatural nucleosides and the unmodified oligonucleotides. 3′-Phosphoramidites of thienopyrimidine and benzodiazepine homo-C-nucleosides were prepared and site-specifically incorporated into DNA. These modified oligonucleotides were hybridized with different DNA and RNA strands in order to study their duplex characteristics in terms of their melting temperatures and circular dichroism spectra.

A versatile approach to alcohol, aldehyde, ketone and amine derivatives starting from β-allyl C-glycosides of D-ribofuranose and 2-deoxy-D-ribofuranose

An efficient preparative procedure is described, leading from β-allyl C-glycosides of d-ribofuranose to alcohols by a hydroboration-oxidation procedure. The corresponding aldehydes were obtained by Swern or Dess-Martin oxidation. Alternatively, two of the alcohols were mesylated to gain access to azides and amines. Treatment of the aldehydes with ethynylmagnesium bromide or phenylethynyllithium and consecutive oxidation of the diastereomeric alcohols provided the acetylenic ketones in good to excellent yields. The obtained derivatives serve as important intermediates for the synthesis of various heterocyclic systems. Georg Thieme Verlag Stuttgart New York.