N³-anisoyl-2'-O-(tetrahydropyran-2-yl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine

Base Information

• Chemical Name: N³-anisoyl-2'-O-(tetrahydropyran-2-yl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine
• CAS No.: 98264-12-1
• Molecular Formula: C₃₄H₅₂N₂O₁₀Si₂
• Molecular Weight: 704.965

Synonyms:N³-anisoyl-2'-O-(tetrahydropyran-2-yl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine

Chemical Property of N³-anisoyl-2'-O-(tetrahydropyran-2-yl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine

Chemical Property:

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Technology Process of N³-anisoyl-2'-O-(tetrahydropyran-2-yl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine

There total 4 articles about N³-anisoyl-2'-O-(tetrahydropyran-2-yl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine 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: 91.0%

2'-O-tetrahydropyranyl-5',3'-O-(tetraisopropyldisiloxane-1,3-diyl)uridine (81243-97-2) + 4-methoxy-benzoyl chloride (100-07-2) → N3-anisoyl-2'-O-(tetrahydropyran-2-yl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine (98264-12-1)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In pyridine; for 10h;

DOI:10.1246/bcsj.58.850

Reference yield:

4-methoxy-benzoyl chloride (100-07-2) → N3-anisoyl-2'-O-(tetrahydropyran-2-yl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine (98264-12-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Na2CO3, tetrabutylammonium bromide / 1.) CH2Cl2, H2O, RT, 2.) 1,2-dichloroethane, Δ

2: CF₃COOH / 1,2-dichloro-ethane / 19 h / Ambient temperature

With tetrabutylammomium bromide; sodium carbonate; trifluoroacetic acid; In 1,2-dichloro-ethane;

DOI:10.1021/jo00271a015

Reference yield:

4-O-<(2,4,6-triisopropylphenyl)sulfonyl>-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine (119694-66-5) → N3-anisoyl-2'-O-(tetrahydropyran-2-yl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine (98264-12-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 6 percent / conc. aq. NH₃ / dioxane / 4 h / Ambient temperature

2: 1.) Na2CO3, tetrabutylammonium bromide / 1.) CH2Cl2, H2O, RT, 2.) 1,2-dichloroethane, Δ

3: CF₃COOH / 1,2-dichloro-ethane / 19 h / Ambient temperature

With ammonium hydroxide; tetrabutylammomium bromide; sodium carbonate; trifluoroacetic acid; In 1,4-dioxane; 1,2-dichloro-ethane;

DOI:10.1021/jo00271a015

upstream raw materials:

2'-O-tetrahydropyranyl-5',3'-O-(tetraisopropyldisiloxane-1,3-diyl)uridine

4-methoxy-benzoyl chloride

4-O-<(2,4,6-triisopropylphenyl)sulfonyl>-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine

3',5'-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine

Downstream raw materials:

N³-anisoyl-2'-O-(tetrahydropyran-2-yl)-5'-O-dimethoxytrityluridine

S,S-diphenyl 2'-O-(tetrahydropyran-2-yl)-N³-anisoyl-uridine 3'phosphorodithioate

S,S-diphenyl 2'-O-(tetrahydropyran-2-yl)-5'-O-(4,4'-dimethoxytrityl)-N³-anisoyluridine-3'-phosphorodithioate

N³-anisoyl-2'-O-(tetrahydropyran-2-yl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine

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