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.: 98889-30-6
• Molecular Formula: C₂₂H₂₆N₂O₉
• Molecular Weight: 462.456

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:

Purity/Quality:

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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 6 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: 90.0%

N3-anisoyl-2'-O-(tetrahydropyran-2-yl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine (98264-12-1) → N3-anisoyl-2'-O-(tetrahydropyran-2-yl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine (98889-30-6)

Guidance literature:

With potassium fluoride; tetraethylammonium bromide; In water; acetonitrile; at 60 ℃; for 5.5h;

DOI:10.1246/bcsj.58.850

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 (98889-30-6)

Guidance literature:

Multi-step reaction with 4 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

4: KF, Et₄NBr / acetonitrile; H₂O / 2.5 h / 60 °C

With potassium fluoride; ammonium hydroxide; tetraethylammonium bromide; tetrabutylammomium bromide; sodium carbonate; trifluoroacetic acid; In 1,4-dioxane; water; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1021/jo00271a015

Reference yield:

3',5'-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine (69304-38-7) → N3-anisoyl-2'-O-(tetrahydropyran-2-yl)-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine (98889-30-6)

Guidance literature:

Multi-step reaction with 3 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

3: KF, Et₄NBr / acetonitrile; H₂O / 2.5 h / 60 °C

With potassium fluoride; tetraethylammonium bromide; tetrabutylammomium bromide; sodium carbonate; trifluoroacetic acid; In water; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1021/jo00271a015

upstream raw materials:

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

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

3,4-dihydro-2H-pyran

4-O-<(2,4,6-triisopropylphenyl)sulfonyl>-3',5'-O-(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

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