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

Base Information

• Chemical Name: S,S-diphenyl 2'-O-(tetrahydropyran-2-yl)-5'-O-(4,4'-dimethoxytrityl)-N³-anisoyluridine-3'-phosphorodithioate
• CAS No.: 86964-78-5
• Molecular Formula: C₅₅H₅₃N₂O₁₂PS₂
• Molecular Weight: 1029.14

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

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

Chemical Property:

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

There total 7 articles about S,S-diphenyl 2'-O-(tetrahydropyran-2-yl)-5'-O-(4,4'-dimethoxytrityl)-N³-anisoyluridine-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: 92.0%

4-methoxy-benzoyl chloride (100-07-2) + 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)-5'-O-(4,4'-dimethoxytrityl)-N3-anisoyluridine-3'-phosphorodithioate (86964-78-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In pyridine; for 15h; Ambient temperature;

DOI:10.1246/cl.1983.1051

Reference yield:

4,4'-dimethoxytrityl chloride (40615-36-9) → S,S-diphenyl 2'-O-(tetrahydropyran-2-yl)-5'-O-(4,4'-dimethoxytrityl)-N3-anisoyluridine-3'-phosphorodithioate (86964-78-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / pyridine / 2.5 h

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

With mesitylene-1,3-disulfonyl dichloride; In pyridine;

DOI:10.1246/bcsj.58.850

Reference yield:

2'-O-tetrahydropyranyl-5',3'-O-(tetraisopropyldisiloxane-1,3-diyl)uridine (81243-97-2) → S,S-diphenyl 2'-O-(tetrahydropyran-2-yl)-5'-O-(4,4'-dimethoxytrityl)-N3-anisoyluridine-3'-phosphorodithioate (86964-78-5)

Guidance literature:

Multi-step reaction with 4 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

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

DOI:10.1246/bcsj.58.850

upstream raw materials:

cyclohexylammonium S,S-diphenyl phosphorodithioate

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

4-methoxy-benzoyl chloride

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

Downstream raw materials:

Thiophosphoric acid O-[(2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-[3-(4-methoxy-benzoyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-4-(tetrahydro-pyran-2-yloxy)-tetrahydro-furan-3-yl] ester S-phenyl ester

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

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