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

Base Information

• Chemical Name: S,S-diphenyl 2'-O-(tetrahydropyran-2-yl)-N³-anisoyl-uridine 3'phosphorodithioate
• CAS No.: 86964-81-0
• Molecular Formula: C₃₄H₃₅N₂O₁₀PS₂
• Molecular Weight: 726.765

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

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

Chemical Property:

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

There total 7 articles about S,S-diphenyl 2'-O-(tetrahydropyran-2-yl)-N³-anisoyl-uridine 3'phosphorodithioate 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%

S,S-diphenyl 2'-O-(tetrahydropyran-2-yl)-5'-O-(4,4'-dimethoxytrityl)-N3-anisoyluridine-3'-phosphorodithioate (86964-78-5) → S,S-diphenyl 2'-O-(tetrahydropyran-2-yl)-N3-anisoyl-uridine 3'phosphorodithioate (86964-81-0)

Guidance literature:

With trifluoroacetic acid; In chloroform; at 0 ℃; for 0.166667h;

DOI:10.1246/cl.1983.1051

Reference yield:

4-methoxy-benzoyl chloride (100-07-2) → S,S-diphenyl 2'-O-(tetrahydropyran-2-yl)-N3-anisoyl-uridine 3'phosphorodithioate (86964-81-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 91 percent / N,N-diisopropylethylamine / pyridine / 10 h

2: 90 percent / tetraethylammonium bromide, potassium fluoride / acetonitrile; H₂O / 5.5 h / 60 °C

3: 74 percent / pyridine / 2.5 h

4: 1.) mesitylene-1,3-disulfonyl dichloride / 1.) pyridine, 30 min, 2.) 75 min

5: 1percent CF₃COOH / CH₂Cl₂ / -10 °C

With potassium fluoride; mesitylene-1,3-disulfonyl dichloride; tetraethylammonium bromide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In pyridine; dichloromethane; water; acetonitrile;

DOI:10.1246/bcsj.58.850

Reference yield:

Dithiophosphoric acid O-[(2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-(tetrahydro-pyran-2-yloxy)-tetrahydro-furan-3-yl] ester S,S'-diphenyl ester (81244-07-7) → S,S-diphenyl 2'-O-(tetrahydropyran-2-yl)-N3-anisoyl-uridine 3'phosphorodithioate (86964-81-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / pyridine, diisopropylethylamine / 14 h

2: 88 percent / 0.5percent TFA / CHCl₃ / 0.07 h / 0 °C

With pyridine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In chloroform;

DOI:10.1021/ja00328a042

upstream raw materials:

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

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

4-methoxy-benzoyl chloride

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

Downstream raw materials:

C₁₃₉H₁₃₇N₁₂O₂₈P₃S₄

C₈₃H₈₂N₄O₂₂P₂S₃

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