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• 55486-09-4 2'-O-Methyl-5-methyluridine 

Relevant academic research and scientific papers

Amide-Linked Ribonucleoside Dimers Derived from S′-Amino-5′-deoxy- and 3′-(Carboxymethyl)-3′-deoxynucleoside Precursors

Treatment of tert-butyldimethylsilyl (TBDMS) derivatives of 3′-keto(adenosine or uridine) with [(ethoxycarbonyl)methylene]triphenylphosphorane gave exocyclic alkenes that underwent stereo-selective hydrogenation to give 3′-deoxy-3′-[(ethoxycarbonyl)methyl](Ado or Urd) analogues. Saponification provided the 3′-(carboxymethyl)-3′-deoxy(Ado and Urd) derivatives 37 and 38. Treatment of 37 or 38 with DCC and 5′-amino-2′,3′-bis-O-TBDMS-5′-deoxynucleosides gave the amide-linked dimers (74-82%). Activation of 37 or 38 with 4-nitrophenol/DCC, and direct coupling of the 4-nitrophenyl esters with 5′-amino-5′-deoxy(Ado or Urd) in pyridine also produced amide dimers efficiently (65-70%). Analogous activation of a 5′-O-DMT-protected carboxylate, and its coupling with 5′-amino-5′-deoxy-2′-O-methyladenosine gave the amide dimer in good yield (74%). Coupling (DCC) of a 5′-azido-2′-O-TBDMS-3′-(carboxymethyl)-3′,5′- dideoxyuridine intermediate with 5′-amino-5′-deoxynucleosides gave amide-linked dimers (72-78%) that can serve as masked (azide reduction) 5′-amino dimers for analogous synthesis of extended amide-linked oligomers.

Synthesis of amide-linked [(3')CH2CO-NH(5')] nucleoside analogues of small oligonucleotides

We report syntheses of new amide-linked (di-penta)nucleoside analogues of antisense oligonucleotide components. Solution-phase coupling of 3'- (carboxymethyl)-3'-deoxy- and 5'-amino-5'-deoxynucleoside derivatives provides amide dimers. Activated [3'-(carboxymethyl)-3'-deoxy] units with a 5'-azido-5'-deoxy function provide 'masked' 5'-amino-5'-deoxy residues for chain extension, and a 5'-O-DMT-protected unit provides the 5'-terminus for attachment to a phosphodiester linkage.