N⁴-benzoyl-1-{2-O-[2,3-di-O-acetyl-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-erythrofuranosyl]-β-D-ribofuranosyl}cytosine

Base Information

• Chemical Name: N⁴-benzoyl-1-{2-O-[2,3-di-O-acetyl-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-erythrofuranosyl]-β-D-ribofuranosyl}cytosine
• CAS No.: 389063-41-6
• Molecular Formula: C₃₆H₅₃N₃O₁₂Si₂
• Molecular Weight: 776.001

Synonyms:N⁴-benzoyl-1-{2-O-[2,3-di-O-acetyl-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-erythrofuranosyl]-β-D-ribofuranosyl}cytosine

Chemical Property of N⁴-benzoyl-1-{2-O-[2,3-di-O-acetyl-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-erythrofuranosyl]-β-D-ribofuranosyl}cytosine

Chemical Property:

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Technology Process of N⁴-benzoyl-1-{2-O-[2,3-di-O-acetyl-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-erythrofuranosyl]-β-D-ribofuranosyl}cytosine

There total 1 articles about N⁴-benzoyl-1-{2-O-[2,3-di-O-acetyl-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-erythrofuranosyl]-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: 51.0%

1,2,3-tri-O-acetyl-D-erythrofuranose (186495-36-3) + 1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl]-N4-benzoylcytosine (69304-43-4) → N4-benzoyl-1-{2-O-[2,3-di-O-acetyl-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-erythrofuranosyl]-β-D-ribofuranosyl}cytosine (389063-41-6)

Guidance literature:

With tin(IV) chloride; In 1,2-dichloro-ethane; at 0 ℃; for 72h;

DOI:10.1002/1522-2675(20010815)84:8<2387::AID-HLCA2387>3.0.CO;2-F

Reference yield: 70.0%

N4-benzoyl-1-{2-O-[2,3-di-O-acetyl-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-erythrofuranosyl]-β-D-ribofuranosyl}cytosine (389063-41-6) → N4-benzoyl-1-[2-O-(2,3-di-O-acetyl-β-D-erythrofuranosyl)-β-D-ribofuranosyl]cytosine (389063-45-0)

Guidance literature:

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

DOI:10.1002/1522-2675(20010815)84:8<2387::AID-HLCA2387>3.0.CO;2-F

Reference yield:

N4-benzoyl-1-{2-O-[2,3-di-O-acetyl-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-erythrofuranosyl]-β-D-ribofuranosyl}cytosine (389063-41-6) → N4-benzoyl-1-[2-O-(2,3-di-O-acetyl-β-D-erythrofuranosyl)-5-O-(dimethoxytrityl)-β-D-ribofuranosyl]cytosine 3'-(2-cyanoethyl diisopropylphosphoramidite)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / Bu₄NF*3H₂O / tetrahydrofuran / 0.25 h / 20 °C

2: 87 percent / pyridine / 2 h / 20 °C

3: 97 percent / iPr₂EtN / CH₂Cl₂ / 1.25 h

With pyridine; tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1002/1522-2675(20010815)84:8<2387::AID-HLCA2387>3.0.CO;2-F

upstream raw materials:

1,2,3-tri-O-acetyl-D-erythrofuranose

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-di-O-acetyl-β-D-erythrofuranosyl)-β-D-ribofuranosyl]cytosine

N⁴-benzoyl-1-[2-O-(2,3-di-O-acetyl-β-D-erythrofuranosyl)-5-O-(dimethoxytrityl)-β-D-ribofuranosyl]cytosine

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