3'-O-(tert-butyldimethylsilyl)-5-fluoro-2'-deoxy-5'-uridyl-2-(4,4,6-trimethyltetrahydro-1,3-oxazin-2-yl)ethyl N-methyl-N-(2-tosylethyl)phosphoramidate

Base Information

Chemical Name:3'-O-(tert-butyldimethylsilyl)-5-fluoro-2'-deoxy-5'-uridyl-2-(4,4,6-trimethyltetrahydro-1,3-oxazin-2-yl)ethyl N-methyl-N-(2-tosylethyl)phosphoramidate
CAS No.:150756-43-7
Molecular Formula:C₃₄H₅₆FN₄O₁₁PSSi
Molecular Weight:806.963
Hs Code.:

3'-O-(tert-butyldimethylsilyl)-5-fluoro-2'-deoxy-5'-uridyl-2-(4,4,6-trimethyltetrahydro-1,3-oxazin-2-yl)ethyl N-methyl-N-(2-tosylethyl)phosphoramidate

Synonyms:3'-O-(tert-butyldimethylsilyl)-5-fluoro-2'-deoxy-5'-uridyl-2-(4,4,6-trimethyltetrahydro-1,3-oxazin-2-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-(4,4,6-trimethyltetrahydro-1,3-oxazin-2-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-(4,4,6-trimethyltetrahydro-1,3-oxazin-2-yl)ethyl N-methyl-N-(2-tosylethyl)phosphoramidate

There total 9 articles about 3'-O-(tert-butyldimethylsilyl)-5-fluoro-2'-deoxy-5'-uridyl-2-(4,4,6-trimethyltetrahydro-1,3-oxazin-2-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:

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

: 150756-43-7
3'-O-(tert-butyldimethylsilyl)-5-fluoro-2'-deoxy-5'-uridyl-2-(4,4,6-trimethyltetrahydro-1,3-oxazin-2-yl)ethyl N-methyl-N-(2-tosylethyl)phosphoramidate

Guidance literature:: Multi-step reaction with 7 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

5: 80percent aq. AcOH / 0.5 h / 80 °C

6: NaIO₄, acetate buffer / tetrahydrofuran / 0.17 h

7: 3 Angstroem molecular sieves / CH₂Cl₂ / 0.25 h

With 1H-imidazole; sodium periodate; acetate buffer; 3 A molecular sieve; acetic acid; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jm00014a019

Reference yield:

: 120957-59-7
3'-O-<(tert-butyl)dimethylsilyl>-2'-deoxy-5-fluorouridine

: 150756-43-7
3'-O-(tert-butyldimethylsilyl)-5-fluoro-2'-deoxy-5'-uridyl-2-(4,4,6-trimethyltetrahydro-1,3-oxazin-2-yl)ethyl N-methyl-N-(2-tosylethyl)phosphoramidate

Guidance literature:: Multi-step reaction with 5 steps

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

2: 92 percent / acetonitrile / 3 h / Heating

3: 80percent aq. AcOH / 0.5 h / 80 °C

4: NaIO₄, acetate buffer / tetrahydrofuran / 0.17 h

5: 3 Angstroem molecular sieves / CH₂Cl₂ / 0.25 h

With sodium periodate; acetate buffer; 3 A molecular sieve; acetic acid; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1021/jm00014a019

Reference yield:

: 150756-38-0
2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl N-methyl-N-(2-bromoethyl)phosphoramidic chloride

: 150756-43-7
3'-O-(tert-butyldimethylsilyl)-5-fluoro-2'-deoxy-5'-uridyl-2-(4,4,6-trimethyltetrahydro-1,3-oxazin-2-yl)ethyl N-methyl-N-(2-tosylethyl)phosphoramidate

Guidance literature:: Multi-step reaction with 5 steps

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

2: 92 percent / acetonitrile / 3 h / Heating

3: 80percent aq. AcOH / 0.5 h / 80 °C

4: NaIO₄, acetate buffer / tetrahydrofuran / 0.17 h

5: 3 Angstroem molecular sieves / CH₂Cl₂ / 0.25 h

With sodium periodate; acetate buffer; 3 A molecular sieve; acetic acid; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1021/jm00014a019