9-[2-O-[2,3-di-O-benzoyl-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-5-O-(phenoxyacetyl)-β-D-ribofuranosyl]-β-D-ribofuranosyl]-N²-isobutyryl guanine

Base Information

• Chemical Name: 9-[2-O-[2,3-di-O-benzoyl-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-5-O-(phenoxyacetyl)-β-D-ribofuranosyl]-β-D-ribofuranosyl]-N²-isobutyryl guanine
• CAS No.: 556039-80-6
• Molecular Formula: C₅₃H₆₇N₅O₁₅Si₂
• Molecular Weight: 1070.31

Synonyms:9-[2-O-[2,3-di-O-benzoyl-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-5-O-(phenoxyacetyl)-β-D-ribofuranosyl]-β-D-ribofuranosyl]-N²-isobutyryl guanine

Chemical Property of 9-[2-O-[2,3-di-O-benzoyl-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-5-O-(phenoxyacetyl)-β-D-ribofuranosyl]-β-D-ribofuranosyl]-N²-isobutyryl guanine

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Technology Process of 9-[2-O-[2,3-di-O-benzoyl-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-5-O-(phenoxyacetyl)-β-D-ribofuranosyl]-β-D-ribofuranosyl]-N²-isobutyryl guanine

There total 1 articles about 9-[2-O-[2,3-di-O-benzoyl-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-5-O-(phenoxyacetyl)-β-D-ribofuranosyl]-β-D-ribofuranosyl]-N²-isobutyryl guanine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 68.0%

3',5'-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-N2-isobutyrylguanosine (87865-78-9) + 1,2,3-tri-O-benzoyl-5-O-(phenoxyacetyl)-D-ribofuranose → 9-[2-O-[2,3-di-O-benzoyl-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-5-O-(phenoxyacetyl)-β-D-ribofuranosyl]-β-D-ribofuranosyl]-N2-isobutyryl guanine (556039-80-6)

Guidance literature:

With tin(IV) chloride; In 1,2-dichloro-ethane; at 0 ℃; for 16h;

DOI:10.1002/hlca.200390050

Reference yield: 68.0%

9-[2-O-[2,3-di-O-benzoyl-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-5-O-(phenoxyacetyl)-β-D-ribofuranosyl]-β-D-ribofuranosyl]-N2-isobutyryl guanine (556039-80-6) → 9-[2-O-(2,3-di-O-benzoyl-β-D-ribofuranosyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl]-N2-isobutyryl guanine (556039-82-8)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 0.166667h;

DOI:10.1002/hlca.200390050

Reference yield:

9-[2-O-[2,3-di-O-benzoyl-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-5-O-(phenoxyacetyl)-β-D-ribofuranosyl]-β-D-ribofuranosyl]-N2-isobutyryl guanine (556039-80-6) → 9-[2-O-(2,3-di-O-benzoyl-5-O-{bis[2-(4-nitrophenyl)ethyl]phosphorylyl}-β-D-ribofuranosyl)-β-D-ribofuranosyl]-N2-isobutyryl guanine (556039-86-2)

Guidance literature:

Multi-step reaction with 3 steps

1: K₂CO₃ / methanol

2: TPSCl; 1-methylimidazole; pyridine

3: Bu₄NF / tetrahydrofuran

With pyridine; 1-methyl-1H-imidazole; Triphenylsilyl chloride; tetrabutyl ammonium fluoride; potassium carbonate; In tetrahydrofuran; methanol;

DOI:10.1081/NCN-120022748

upstream raw materials:

3',5'-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-N₂-isobutyrylguanosine

Downstream raw materials:

9-[2-O-(2,3-di-O-benzoyl-β-D-ribofuranosyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl]-N²-isobutyryl guanine

9-[2-O-(2,3-di-O-benzoyl-5-O-{bis[2-(4-nitrophenyl)ethyl]phosphorylyl}-β-D-ribofuranosyl)-β-D-ribofuranosyl]-N²-isobutyryl guanine

9-[2-O-[2,3-di-O-benzoyl-5-O-bis[2-(4-nitrophenyl)ethyl]phosphorylyl-β-D-ribofuranosyl]-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl]-N²-isobutyryl guanine

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