N⁴-benzoyl-1-[3,5-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-β-D-ribofuranosyl]cytosine

Base Information

• Chemical Name: N⁴-benzoyl-1-[3,5-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-β-D-ribofuranosyl]cytosine
• CAS No.: 169687-75-6
• Molecular Formula: C₅₄H₆₃N₃O₁₄Si₂
• Molecular Weight: 1034.28

Synonyms:N⁴-benzoyl-1-[3,5-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-β-D-ribofuranosyl]cytosine

Chemical Property of N⁴-benzoyl-1-[3,5-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-β-D-ribofuranosyl]cytosine

Chemical Property:

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Technology Process of N⁴-benzoyl-1-[3,5-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-β-D-ribofuranosyl]cytosine

There total 1 articles about N⁴-benzoyl-1-[3,5-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-β-D-ribofuranosyl]cytosine 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: 80.0%

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (6974-32-9) + 1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl]-N4-benzoylcytosine (69304-43-4) → N4-benzoyl-1-[3,5-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-β-D-ribofuranosyl]cytosine (169687-75-6)

Guidance literature:

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose; With tin(IV) chloride; In 1,2-dichloro-ethane; at 0 ℃; for 0.166667h;

1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl]-N⁴-benzoylcytosine; In 1,2-dichloro-ethane; at 0 ℃; for 2h;

DOI:10.1080/07328309708006511

Reference yield: 95.0%

N4-benzoyl-1-[3,5-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-β-D-ribofuranosyl]cytosine (169687-75-6) → N4-benzoyl-1-[2-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-β-D-ribofuranosyl]cytosine (183281-88-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.25h;

DOI:10.1080/07328309708006511

Reference yield:

N4-benzoyl-1-[3,5-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-β-D-ribofuranosyl]cytosine (169687-75-6) → N4-benzoyl-1-[5-O-(4,4'-dimethoxytrityl)-2-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-β-D-ribofuranosyl]cytosine (183282-02-2)

Guidance literature:

Multi-step reaction with 2 steps

1: TBAF / tetrahydrofuran / 0.33 h

2: pyridine / 2 h

With pyridine; tetrabutyl ammonium fluoride; In tetrahydrofuran;

upstream raw materials:

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl]-N⁴-benzoylcytosine

Downstream raw materials:

N⁴-benzoyl-1-[2-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-β-D-ribofuranosyl]cytosine

C₃₅H₃₃N₃O₁₂

N⁴-benzoyl-1-[5-O-(4,4'-dimethoxytrityl)-2-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-β-D-ribofuranosyl]cytosine

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