5′-O-(4,4′-dimethoxytrityl)-2′-O-(tert-butyldimethylsilyl)-4-(2-cyanoethylthio)uridine

Base Information

• Chemical Name: 5′-O-(4,4′-dimethoxytrityl)-2′-O-(tert-butyldimethylsilyl)-4-(2-cyanoethylthio)uridine
• CAS No.: 154665-03-9
• Molecular Formula: C₃₉H₄₇N₃O₇SSi
• Molecular Weight: 729.97

Synonyms:5′-O-(4,4′-dimethoxytrityl)-2′-O-(tert-butyldimethylsilyl)-4-(2-cyanoethylthio)uridine

Chemical Property of 5′-O-(4,4′-dimethoxytrityl)-2′-O-(tert-butyldimethylsilyl)-4-(2-cyanoethylthio)uridine

Chemical Property:

Purity/Quality:

98%min ^*data from raw suppliers

3-((1-((2R,3R,4R,5R)-5-((Bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3-((tert-butyldimethylsilyl)oxy)-4-hydroxytetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)thio)propanenitrile 95% ^*data from reagent suppliers

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Technology Process of 5′-O-(4,4′-dimethoxytrityl)-2′-O-(tert-butyldimethylsilyl)-4-(2-cyanoethylthio)uridine

There total 18 articles about 5′-O-(4,4′-dimethoxytrityl)-2′-O-(tert-butyldimethylsilyl)-4-(2-cyanoethylthio)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: 80.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + 2′-O-(tert-butyldimethylsilyl)-4-(2-cyanoethylthio)uridine (293300-80-8) → 5′-O-(4,4′-dimethoxytrityl)-2′-O-(tert-butyldimethylsilyl)-4-(2-cyanoethylthio)uridine (154665-03-9)

Guidance literature:

With pyridine; at 20 ℃; for 18h;

DOI:10.1002/anie.201707465

Reference yield: 40.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 4-S-(2-cyanoethyl)-5'-O-(4,4'-dimethoxytrityl)-4-thiouridine (170660-46-5) → 5′-O-(4,4′-dimethoxytrityl)-2′-O-(tert-butyldimethylsilyl)-4-(2-cyanoethylthio)uridine (154665-03-9)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 36h;

DOI:10.1021/jo991432z

Reference yield: 16.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 4-S-(2-cyanoethyl)-5'-O-(4,4'-dimethoxytrityl)-4-thiouridine (170660-46-5) → 3-{1-[(2R,3R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-ylsulfanyl}-propionitrile + 5′-O-(4,4′-dimethoxytrityl)-2′-O-(tert-butyldimethylsilyl)-4-(2-cyanoethylthio)uridine (154665-03-9)

Guidance literature:

With pyridine; for 60h;

DOI:10.1016/S0040-4039(00)75812-6

upstream raw materials:

tert-butyldimethylsilyl chloride

4-S-(2-cyanoethyl)-5'-O-(4,4'-dimethoxytrityl)-4-thiouridine

3-mercaptopropionitrile

S-(2-cyanoethyl)-4-thiouridine

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