N⁶-benzoyl-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]adenine

Base Information

• Chemical Name: N⁶-benzoyl-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]adenine
• CAS No.: 556039-81-7
• Molecular Formula: C₅₆H₆₅N₅O₁₄Si₂
• Molecular Weight: 1088.33

Synonyms:N⁶-benzoyl-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]adenine

Chemical Property of N⁶-benzoyl-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]adenine

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Technology Process of N⁶-benzoyl-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]adenine

There total 1 articles about N⁶-benzoyl-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]adenine 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: 60.0%

3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-N6-benzoyladenosine (79154-57-7) + 1,2,3-tri-O-benzoyl-5-O-(phenoxyacetyl)-D-ribofuranose → N6-benzoyl-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]adenine (556039-81-7)

Guidance literature:

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

DOI:10.1002/hlca.200390050

Reference yield: 63.0%

N6-benzoyl-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]adenine (556039-81-7) → N6-benzoyl-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]adenine (556039-83-9)

Guidance literature:

With potassium carbonate; In methanol;

DOI:10.1002/hlca.200390050

Reference yield:

N6-benzoyl-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]adenine (556039-81-7) → N6-benzoyl-9-[2-O-(2,3-di-O-benzoyl-5-O-{bis[2-(4-nitrophenyl)ethyl]phosphorylyl}-β-D-ribofuranosyl)-β-D-ribofuranosyl]adenine (556039-87-3)

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-(tetraisopropyldisiloxane-1,3-diyl)-N₆-benzoyladenosine

Downstream raw materials:

N⁶-benzoyl-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]adenine

O-β-D-ribofuranosyl-(1''-2')-adenosine-5''-O-phosphate

N⁶-benzoyl-9-[2-O-(2,3-di-O-benzoyl-5-O-{bis[2-(4-nitrophenyl)ethyl]phosphorylyl}-β-D-ribofuranosyl)-β-D-ribofuranosyl]adenine

N⁶-benzoyl-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]adenine

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