1-[2,5-di-O-(tert-butyldimethylsilyl)-3-C-(2-phenylselenylethyl)-β-D-ribo-pentofuranosyl]uracil

Base Information

Chemical Name:1-[2,5-di-O-(tert-butyldimethylsilyl)-3-C-(2-phenylselenylethyl)-β-D-ribo-pentofuranosyl]uracil
CAS No.:887486-85-3
Molecular Formula:C₂₉H₄₈N₂O₆SeSi₂
Molecular Weight:655.841
Hs Code.:

Synonyms:1-[2,5-di-O-(tert-butyldimethylsilyl)-3-C-(2-phenylselenylethyl)-β-D-ribo-pentofuranosyl]uracil

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Chemical Property of 1-[2,5-di-O-(tert-butyldimethylsilyl)-3-C-(2-phenylselenylethyl)-β-D-ribo-pentofuranosyl]uracil

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Technology Process of 1-[2,5-di-O-(tert-butyldimethylsilyl)-3-C-(2-phenylselenylethyl)-β-D-ribo-pentofuranosyl]uracil

There total 7 articles about 1-[2,5-di-O-(tert-butyldimethylsilyl)-3-C-(2-phenylselenylethyl)-β-D-ribo-pentofuranosyl]uracil 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: 98.0%

: 887486-83-1
1-[2,5-di-O-(tert-butyldimethylsilyl)-3-C-(2-mesyloxyethyl)-β-D-ribo-pentofuranosyl]uracil

: 1666-13-3
diphenyl diselenide

: 887486-85-3
1-[2,5-di-O-(tert-butyldimethylsilyl)-3-C-(2-phenylselenylethyl)-β-D-ribo-pentofuranosyl]uracil

Guidance literature:: diphenyl diselenide; With sodium tetrahydroborate; In ethanol; at 20 ℃; for 0.25h;

1-[2,5-di-O-(tert-butyldimethylsilyl)-3-C-(2-mesyloxyethyl)-β-D-ribo-pentofuranosyl]uracil; In ethanol; at 60 ℃; for 1h;
DOI:10.1039/b517602f

Reference yield:

: [4-(tert-butyl-dimethyl-silanyloxy)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-yl]-acetic acid methyl ester

: 887486-85-3
1-[2,5-di-O-(tert-butyldimethylsilyl)-3-C-(2-phenylselenylethyl)-β-D-ribo-pentofuranosyl]uracil

Guidance literature:: Multi-step reaction with 4 steps

1.1: 2.30 g / imidazole / dimethylformamide / 0.5 h / 20 °C

2.1: 39 percent / DIBAL-H / tetrahydrofuran; hexane / 2 h / 0 °C

3.1: 92 percent / DMAP; Et₃N / CH₂Cl₂ / 0.5 h / 20 °C

4.1: NaBH₄ / ethanol / 0.25 h / 20 °C

4.2: 98 percent / ethanol / 1 h / 60 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1039/b517602f

Reference yield:

: 887486-81-9
1-[2,5-di-O-(tert-butyldimethylsilyl)-3-C-(2-hydroxyethyl)-β-D-ribo-pentofuranosyl]uracil

: 887486-85-3
1-[2,5-di-O-(tert-butyldimethylsilyl)-3-C-(2-phenylselenylethyl)-β-D-ribo-pentofuranosyl]uracil

Guidance literature:: Multi-step reaction with 2 steps

1.1: 92 percent / DMAP; Et₃N / CH₂Cl₂ / 0.5 h / 20 °C

2.1: NaBH₄ / ethanol / 0.25 h / 20 °C

2.2: 98 percent / ethanol / 1 h / 60 °C

With dmap; sodium tetrahydroborate; triethylamine; In ethanol; dichloromethane;
DOI:10.1039/b517602f