N³-[(triphenylmethyl)sulfenyl]-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine

Base Information

• Chemical Name: N³-[(triphenylmethyl)sulfenyl]-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine
• CAS No.: 117901-68-5
• Molecular Formula: C₄₀H₅₂N₂O₇SSi₂
• Molecular Weight: 761.099

Synonyms:N³-[(triphenylmethyl)sulfenyl]-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine

Chemical Property of N³-[(triphenylmethyl)sulfenyl]-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine

Chemical Property:

Purity/Quality:

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Technology Process of N³-[(triphenylmethyl)sulfenyl]-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine

There total 2 articles about N³-[(triphenylmethyl)sulfenyl]-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: 98.0%

tritylsulfenyl chloride (24165-03-5) + 3',5'-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine (69304-38-7) → N3-[(triphenylmethyl)sulfenyl]-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine (117901-68-5)

Guidance literature:

With tetrabutylammomium bromide; sodium carbonate; In dichloromethane; water; for 2h; Ambient temperature;

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-[(triphenylmethyl)sulfenyl]-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine (117901-68-5)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 98 percent / Na₂CO₃, tetrabutylammonium bromide / CH₂Cl₂; H₂O / 2 h / Ambient temperature

With ammonium hydroxide; tetrabutylammomium bromide; sodium carbonate; In 1,4-dioxane; dichloromethane; water;

DOI:10.1021/jo00271a015

Reference yield: 78.0%

bromoacetic acid tert-butyl ester (5292-43-3) + N3-[(triphenylmethyl)sulfenyl]-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine (117901-68-5) → [(2R,3R,3aR,9aR)-2-(2,4-Dioxo-3-tritylsulfanyl-3,4-dihydro-2H-pyrimidin-1-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yloxy]-acetic acid tert-butyl ester (156703-93-4)

Guidance literature:

With sodium hydride; In tetrahydrofuran; for 0.5h;

upstream raw materials:

tritylsulfenyl chloride

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

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

Downstream raw materials:

[(2R,3R,3aR,9aR)-2-(2,4-Dioxo-3-tritylsulfanyl-3,4-dihydro-2H-pyrimidin-1-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yloxy]-acetic acid tert-butyl ester

[(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-tetrahydro-furan-3-yloxy]-acetic acid

[(2R,3R,4R,5R)-2-(2,4-Dioxo-3-tritylsulfanyl-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yloxy]-acetic acid tert-butyl ester

[(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-tetrahydro-furan-3-yloxy]-acetic acid tert-butyl ester

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