76700-77-1

Upstream product

• 18173-84-7 diisopropylsilanol 
• 18043-71-5 1,1,3,3-tetraisopropyldisiloxane 
• 69304-37-6 1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane 
• 108-95-2 phenol 
• 58-61-7 adenosine 
• 69304-45-6 3',5'-O-(1,1,3,3-tetra-isopropyldisiloxane-1,3-diyl)adenosine 
• 1005-56-7 phenylcarbonochloridothioate 

Downstream Products

• 1276113-12-2 N6-benzoyl-2'-deoxy-2'-C-α-(hydroxymethyl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)adenosine 
• 1276113-10-0 N6-benzoyl-2'-deoxy-α-C-(1-phenylethane-1,2-diol)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)adenosine 
• 958-09-8 2'-deoxy-D-adenosine 

Relevant academic research and scientific papers

A solid-state deuterium NMR study of furanose ring dynamics in [d(CGCGAATTCGCG)]2

Solid-state deuterium NMR spectroscopy has been used to characterize the dynamics of the furanose rings of A5 and A6 (and by symmetry A17 and A18) in the self-complementary DNA dodecamer duplex [d(CGCGAATTCGCG)]2, which contains the EcoRI bindi

2′-deoxy-2′-α-C-(hydroxymethyl)adenosine as potential anti-HCV agent

Because of the importance of C-branched nucleosides in the discovery of new antiviral molecules, we decided to synthesize 2′-deoxy-2′-α- C-(hydroxymethyl)adenosine as a potential anti-HCV agent. The synthesis of a new adenosine analogue following two different synthetic routes is described. The new C-branched nucleoside was tested for its antiviral activity and found to be inactive.

Synthesis of 2'-Allyl-2'-Deoxynucleosides by Radical Reactions

2'-α-Allyl-2'-deoxynucleosides derived from uridine, cytidine, adenosine and guanosine have been synthesized in high overall yields by photolysis of appropriately protected 2'-O-phenoxythiocarbonyl derivatives in the presence of allyltributylstannane.The 2'-allyl-2'-deoxynucleosides were 5'-O-DMT-protected and converted into 2'-deoxynucleoside 3'-O-phosphoramidites to serve as monomers for oligonucleotides.

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.