187733-73-9

Upstream product

• 251296-62-5 3',5'-bis-O-(tert-butyldimethylsilyl)-2'-O-methyl-5-methyluridine 
• 251297-03-7 3'-O-TBDMS-2'-O-methyl-5-methylUrd 
• 251296-64-7 3'-O-(tert-butyldimethylsilyl)-5'-chloro-5'-deoxy-2'-O-methyl-5-methyluridine 
• 133023-98-0 3-N-benzoyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-O-methyl-5-methyluridine 
• 166593-44-8 1-<3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-methyl-β-D-ribofuranos-1-yl>thymine 
• 55486-09-4 2'-O-Methyl-5-methyluridine 
• 131132-30-4 N³-benzoyl-3′,5′-O-(1,1,3,3-tetraisopropyl disiloxane-1,3-diyl)5-methyluridine 
• 268747-99-5 5'-chloro-5'-deoxy-2'-O-methyl-5-methyluridine 
• 251296-66-9 5'-azido-3'-O-(tert-butyldimethylsilyl)-5'-deoxy-2'-O-methyl-5-methyluridine 
• 187733-72-8 1-((2R,3R,4S,5S)-4-Hydroxy-5-iodomethyl-3-methoxy-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione 

Downstream Products

• 171762-81-5 C₅₅H₆₇N₅O₁₀Si₂ 
• 171762-83-7 C₄₄H₄₉N₅O₁₂ 
• 187733-63-7 C₅₅H₆₇N₅O₁₀Si₂ 
• 171762-61-1 C₄₄H₄₉N₅O₁₂ 
• 187733-60-4 1-[(2R,3R,4R,5R)-5-Aminomethyl-4-(tert-butyl-diphenyl-silanyloxy)-3-methoxy-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 
• 452096-04-7 C₆₃H₇₇N₆O₁₁PSi₂ 
• 197022-33-6 C₄₅H₅₄N₅O₁₃P 
• 197022-34-7 C₄₅H₅₄N₅O₁₃P 
• 197021-58-2 N-{1-[5-azidomethyl-4-(tert-butyl-diphenyl-silanyloxy)-3-methoxy-tetrahydro-furan-2-yl]-5-methyl-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide 
• 452096-06-9 1-[5-azidomethyl-4-(tert-butyl-diphenyl-silanyloxy)-3-methoxy-tetrahydro-furan-2-yl]-5-methyl-4-[1,2,4]triazol-1-yl-1H-pyrimidin-2-one 
• 171762-85-9 4-Amino-1-[(2R,3R,4R,5R)-5-azidomethyl-4-(tert-butyl-diphenyl-silanyloxy)-3-methoxy-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidin-2-one 
• 171763-28-3 1-[(2R,3R,4R,5R)-5-Azidomethyl-4-(tert-butyl-diphenyl-silanyloxy)-3-methoxy-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 

Relevant academic research and scientific papers

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.

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.

Stark erhoehte Affinitaet modifizierter Oligonucleotide mit in ihrer Konformation eingeschraenkten Furanose-Ringen fuer komplementaere RNA-Straenge

Keywords: Amide; Antisense-Oligonucleotide; Desoxyzucker; Molekular Modeling; Nucleinsaeuren