3'-O-(tert-butyldimethylsilyl)-5-fluoro-2'-deoxy-5'-uridyl 2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl N-methyl-N-(2-tosylethyl)phosphoramidate

Base Information

Chemical Name:3'-O-(tert-butyldimethylsilyl)-5-fluoro-2'-deoxy-5'-uridyl 2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl N-methyl-N-(2-tosylethyl)phosphoramidate
CAS No.:150756-42-6
Molecular Formula:C₃₂H₅₁FN₃O₁₂PSSi
Molecular Weight:779.894
Hs Code.:

Synonyms:3'-O-(tert-butyldimethylsilyl)-5-fluoro-2'-deoxy-5'-uridyl 2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl N-methyl-N-(2-tosylethyl)phosphoramidate

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Chemical Property of 3'-O-(tert-butyldimethylsilyl)-5-fluoro-2'-deoxy-5'-uridyl 2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl N-methyl-N-(2-tosylethyl)phosphoramidate

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Technology Process of 3'-O-(tert-butyldimethylsilyl)-5-fluoro-2'-deoxy-5'-uridyl 2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl N-methyl-N-(2-tosylethyl)phosphoramidate

There total 7 articles about 3'-O-(tert-butyldimethylsilyl)-5-fluoro-2'-deoxy-5'-uridyl 2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl N-methyl-N-(2-tosylethyl)phosphoramidate 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%

: 16836-95-6
silver(I) 4-methylbenzenesulfonate

: 150756-39-1
3'-O-(tert-butyldimethylsilyl)-5-fluoro-2'-deoxy-5'-uridyl 2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl N-methyl-N-(2-bromoethyl)phosphoramidate

: 150756-42-6
3'-O-(tert-butyldimethylsilyl)-5-fluoro-2'-deoxy-5'-uridyl 2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl N-methyl-N-(2-tosylethyl)phosphoramidate

Guidance literature:: In acetonitrile; for 3h; Heating;
DOI:10.1021/jm00014a019

Reference yield:

: 5754-34-7
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

: 150756-42-6
3'-O-(tert-butyldimethylsilyl)-5-fluoro-2'-deoxy-5'-uridyl 2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl N-methyl-N-(2-tosylethyl)phosphoramidate

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) BuLi / 1.) -78 deg C, THF, 2.) -78 deg C, THF, 3 h

2: 1.) LDA / 1.) THF, 2.) THF, RT, overnight

3: 92 percent / acetonitrile / 3 h / Heating

With n-butyllithium; lithium diisopropyl amide; In acetonitrile;
DOI:10.1021/jm00014a019

Reference yield:

: 4031-24-7,10343-71-2,103285-11-6
1-(2-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)-5-fluorouracil

: 150756-42-6
3'-O-(tert-butyldimethylsilyl)-5-fluoro-2'-deoxy-5'-uridyl 2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl N-methyl-N-(2-tosylethyl)phosphoramidate

Guidance literature:: Multi-step reaction with 4 steps

1: imidazole / dimethylformamide / Ambient temperature

2: 80percent aq. AcOH / 0.5 h / Heating

3: 1.) LDA / 1.) THF, 2.) THF, RT, overnight

4: 92 percent / acetonitrile / 3 h / Heating

With 1H-imidazole; acetic acid; lithium diisopropyl amide; In N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jm00014a019