5'-O-[benzhydryloxy-bis(trimethylsilyloxy)silyl]-2'-O-[bis(2-acetoxyethoxy)methyl]-3-methyluridine

Base Information

• Chemical Name: 5'-O-[benzhydryloxy-bis(trimethylsilyloxy)silyl]-2'-O-[bis(2-acetoxyethoxy)methyl]-3-methyluridine
• CAS No.: 415903-59-2
• Molecular Formula: C₃₈H₅₆N₂O₁₅Si₃
• Molecular Weight: 865.124
• Mol file: 415903-59-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about 5'-O-[benzhydryloxy-bis(trimethylsilyloxy)silyl]-2'-O-[bis(2-acetoxyethoxy)methyl]-3-methyluridine 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: 86.0%

benzhydryloxy-bis(trimethylsilyloxy)silyl chloride (309963-45-9) + 2'-O-[bis(2-acetoxyethoxy)methyl]-3-methyluridine (415903-56-9) → 5'-O-[benzhydryloxy-bis(trimethylsilyloxy)silyl]-2'-O-[bis(2-acetoxyethoxy)methyl]-3-methyluridine (415903-59-2)

Guidance literature:

With diisopropylamine; In dichloromethane; at 0 ℃;

DOI:10.1016/S0968-0896(01)00283-8

Reference yield:

3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-2'-O-(trimethylsilyl)uridine (415903-48-9) → 5'-O-[benzhydryloxy-bis(trimethylsilyloxy)silyl]-2'-O-[bis(2-acetoxyethoxy)methyl]-3-methyluridine (415903-59-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 93 percent / benzene / 7 h / Heating

2.1: 100 percent / p-TsOH*H₂O / tetrahydrofuran / 1.5 h / 20 °C

3.1: pyridinium p-toluenesulfonate / CH₂Cl₂ / 2 h / 20 °C

3.2: 88 percent / 4-(tert-butyldimethylsilyloxy)-3-penten-2-one / CH₂Cl₂ / 48 h / 20 °C

4.1: 93 percent / TMEDA; aq. HF / acetonitrile / 0 - 20 °C

5.1: 86 percent / diisopropylamine / CH₂Cl₂ / 0 °C

With N,N,N,N,-tetramethylethylenediamine; hydrogen fluoride; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; diisopropylamine; In tetrahydrofuran; dichloromethane; acetonitrile; benzene;

DOI:10.1016/S0968-0896(01)00283-8

Reference yield:

uridine (58-96-8) → 5'-O-[benzhydryloxy-bis(trimethylsilyloxy)silyl]-2'-O-[bis(2-acetoxyethoxy)methyl]-3-methyluridine (415903-59-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 83 percent / pyridine / 6 h / 0 - 20 °C

2.1: Et₃N / CH₂Cl₂ / 3.5 h / 0 - 20 °C

3.1: 93 percent / benzene / 7 h / Heating

4.1: 100 percent / p-TsOH*H₂O / tetrahydrofuran / 1.5 h / 20 °C

5.1: pyridinium p-toluenesulfonate / CH₂Cl₂ / 2 h / 20 °C

5.2: 88 percent / 4-(tert-butyldimethylsilyloxy)-3-penten-2-one / CH₂Cl₂ / 48 h / 20 °C

6.1: 93 percent / TMEDA; aq. HF / acetonitrile / 0 - 20 °C

7.1: 86 percent / diisopropylamine / CH₂Cl₂ / 0 °C

With N,N,N,N,-tetramethylethylenediamine; hydrogen fluoride; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; triethylamine; diisopropylamine; In tetrahydrofuran; pyridine; dichloromethane; acetonitrile; benzene;

DOI:10.1016/S0968-0896(01)00283-8

upstream raw materials:

benzhydryloxy-bis(trimethylsilyloxy)silyl chloride

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

3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-2'-O-(trimethylsilyl)uridine

uridine