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Atomfair (2R,3R,4R,5R)-5-(4-Acetamido-2-oxopyrimidin-1(2H)-yl)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-(prop-2-yn-1-yloxy)tetrahydrofuran-3-yl (2-cyanoethyl) diisopropylphosphoramidite 2′-propargyl C(Ac) amidite, BP-43342, H39099 C44H52N5O9P CAS 1498305-51-3

(2R,3R,4R,5R)-5-(4-Acetamido-2-oxopyrimidin-1(2H)-yl)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-(prop-2-yn-1-yloxy)tetrahydrofuran-3-yl (2-cyanoethyl) diisopropylphosphoramidite (CAS No. 1498305-51-3) is a high-purity phosphoramidite monomer designed for oligonucleotide synthesis, particularly for introducing propargyl-modified nucleosides. With the molecular formula C44H52N5O9P , this compound features a 2′-propargyloxy modification on the ribose sugar, enabling click chemistry applications such as CuAAC (copper-catalyzed azide-alkyne cycloaddition). The molecule is protected with a DMTr (4,4′-dimethoxytrityl) group at the 5′-position and a cyanoethyl-diisopropylphosphoramidite moiety at the 3′-position, ensuring compatibility with automated solid-phase DNA/RNA synthesizers. This reagent is ideal for researchers developing functionalized oligonucleotides for diagnostics, therapeutics, or bioconjugation.

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Description

(2R,3R,4R,5R)-5-(4-Acetamido-2-oxopyrimidin-1(2H)-yl)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-(prop-2-yn-1-yloxy)tetrahydrofuran-3-yl (2-cyanoethyl) diisopropylphosphoramidite (CAS No. 1498305-51-3) is a high-purity phosphoramidite monomer designed for oligonucleotide synthesis, particularly for introducing propargyl-modified nucleosides. With the molecular formula C44H52N5O9P, this compound features a 2′-propargyloxy modification on the ribose sugar, enabling click chemistry applications such as CuAAC (copper-catalyzed azide-alkyne cycloaddition). The molecule is protected with a DMTr (4,4′-dimethoxytrityl) group at the 5′-position and a cyanoethyl-diisopropylphosphoramidite moiety at the 3′-position, ensuring compatibility with automated solid-phase DNA/RNA synthesizers. This reagent is ideal for researchers developing functionalized oligonucleotides for diagnostics, therapeutics, or bioconjugation.

Properties

  • CAS Number: 1498305-51-3
  • Complexity: 1490
  • IUPAC Name: N-[1-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenyl-methoxy]methyl]-4-[2-cyanoethoxy-(diisopropylamino)phosphanyl]oxy-3-prop-2-ynoxy-tetrahydrofuran-2-yl]-2-oxo-pyrimidin-4-yl]acetamide
  • InChI: InChI=1S/C44H52N5O9P/c1-9-27-54-41-40(58-59(56-28-13-25-45)49(30(2)3)31(4)5)38(57-42(41)48-26-24-39(46-32(6)50)47-43(48)51)29-55-44(33-14-11-10-12-15-33,34-16-20-36(52-7)21-17-34)35-18-22-37(53-8)23-19-35/h1,10-12,14-24,26,30-31,38,40-42H,13,27-29H2,2-8H3,(H,46,47,50,51)/t38-,40-,41-,42-,59?/m1/s1
  • InChI Key: JIMYWWYYWAHJAD-ZMHKPELYSA-N
  • Exact Mass: 825.35026525
  • Molecular Formula: C44H52N5O9P
  • Molecular Weight: 825.9
  • SMILES: CC(C)N(C(C)C)P(OCCC#N)O[C@@H]1[C@H](O[C@H]([C@@H]1OCC#C)N2C=CC(=NC2=O)NC(=O)C)COC(C3=CC=CC=C3)(C4=CC=C(C=C4)OC)C5=CC=C(C=C5)OC
  • Topological: 153
  • Monoisotopic Mass: 825.35026525
  • Synonyms: 1498305-51-3, (2R,3R,4R,5R)-5-(4-Acetamido-2-oxopyrimidin-1(2H)-yl)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-(prop-2-yn-1-yloxy)tetrahydrofuran-3-yl (2-cyanoethyl) diisopropylphosphoramidite, 2′-propargyl C(Ac) amidite, BP-43342, H39099

Application

This phosphoramidite is widely used in the synthesis of propargyl-modified oligonucleotides for click chemistry-based labeling, such as fluorescent tagging or bioconjugation with azide-bearing molecules. It enables the incorporation of alkyne handles into nucleic acids for applications like bioorthogonal chemistry, probe development, and nanostructure assembly. The compound is particularly valuable in chemical biology and therapeutic oligonucleotide research, where site-specific modifications are critical.

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Disclaimer

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