5'-O-[benzhydryloxybis(trimethylsilyloxy)silyl]-2'-O-[bis(2-acetoxyethoxy)methyl]-3-methylpseudouridine

Base Information

• Chemical Name: 5'-O-[benzhydryloxybis(trimethylsilyloxy)silyl]-2'-O-[bis(2-acetoxyethoxy)methyl]-3-methylpseudouridine
• CAS No.: 482643-97-0
• Molecular Formula: C₃₈H₅₆N₂O₁₅Si₃
• Molecular Weight: 865.124
• Mol file: 482643-97-0.mol

Synonyms:5'-O-[benzhydryloxybis(trimethylsilyloxy)silyl]-2'-O-[bis(2-acetoxyethoxy)methyl]-3-methylpseudouridine

Chemical Property of 5'-O-[benzhydryloxybis(trimethylsilyloxy)silyl]-2'-O-[bis(2-acetoxyethoxy)methyl]-3-methylpseudouridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5'-O-[benzhydryloxybis(trimethylsilyloxy)silyl]-2'-O-[bis(2-acetoxyethoxy)methyl]-3-methylpseudouridine

There total 8 articles about 5'-O-[benzhydryloxybis(trimethylsilyloxy)silyl]-2'-O-[bis(2-acetoxyethoxy)methyl]-3-methylpseudouridine 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: 68.0%

benzhydryloxy-bis(trimethylsilyloxy)silyl chloride (309963-45-9) + 2'-O-[bis(2-acetoxyethoxy)methyl]-3-methylpseudouridine (482643-94-7) → 5'-O-[benzhydryloxybis(trimethylsilyloxy)silyl]-2'-O-[bis(2-acetoxyethoxy)methyl]-3-methylpseudouridine (482643-97-0)

Guidance literature:

With diisopropylamine; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1021/jo026364m

Reference yield:

3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-2'-O-(trimethylsilyl)pseudouridine (164300-60-1) → 5'-O-[benzhydryloxybis(trimethylsilyloxy)silyl]-2'-O-[bis(2-acetoxyethoxy)methyl]-3-methylpseudouridine (482643-97-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 30 percent Chromat_. / K₂CO₃ / dimethylsulfoxide / 12 h / 20 °C

2.1: 98 percent / benzene / 6 h / Heating

3.1: 92 percent / methanolic ammonia / 0 - 20 °C

4.1: pyridinium p-toluenesulfonate / dioxane / 1 h

4.2: 69 percent / 4-(tert-butyldimethylsilyloxy)-3-penten-2-one / dioxane / 20 - 40 °C

5.1: 585 mg / TMEDA; aq. HF / acetonitrile / 0 - 20 °C

6.1: 68 percent / diisopropylamine / CH₂Cl₂ / 2 h / 0 °C

With N,N,N,N,-tetramethylethylenediamine; hydrogen fluoride; ammonia; pyridinium p-toluenesulfonate; potassium carbonate; diisopropylamine; In 1,4-dioxane; dichloromethane; dimethyl sulfoxide; acetonitrile; benzene;

DOI:10.1021/jo026364m

Reference yield:

3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)pseudouridine (80545-49-9) → 5'-O-[benzhydryloxybis(trimethylsilyloxy)silyl]-2'-O-[bis(2-acetoxyethoxy)methyl]-3-methylpseudouridine (482643-97-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 99 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

2.1: 30 percent Chromat_. / K₂CO₃ / dimethylsulfoxide / 12 h / 20 °C

3.1: 98 percent / benzene / 6 h / Heating

4.1: 92 percent / methanolic ammonia / 0 - 20 °C

5.1: pyridinium p-toluenesulfonate / dioxane / 1 h

5.2: 69 percent / 4-(tert-butyldimethylsilyloxy)-3-penten-2-one / dioxane / 20 - 40 °C

6.1: 585 mg / TMEDA; aq. HF / acetonitrile / 0 - 20 °C

7.1: 68 percent / diisopropylamine / CH₂Cl₂ / 2 h / 0 °C

With N,N,N,N,-tetramethylethylenediamine; hydrogen fluoride; ammonia; pyridinium p-toluenesulfonate; potassium carbonate; triethylamine; diisopropylamine; In 1,4-dioxane; dichloromethane; dimethyl sulfoxide; acetonitrile; benzene;

DOI:10.1021/jo026364m

upstream raw materials:

benzhydryloxy-bis(trimethylsilyloxy)silyl chloride

2'-O-[bis(2-acetoxyethoxy)methyl]-3-methylpseudouridine

3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)pseudouridine

3-methyl-3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)pseudouridine