1-[3-C-ethynyl-2-O-[phenoxy(thiocarbonyl)]-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribo-pentofuranosyl]uracil

Base Information

Chemical Name:1-[3-C-ethynyl-2-O-[phenoxy(thiocarbonyl)]-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribo-pentofuranosyl]uracil
CAS No.:197298-02-5
Molecular Formula:C₃₀H₄₂N₂O₈SSi₂
Molecular Weight:646.909
Hs Code.:

Synonyms:1-[3-C-ethynyl-2-O-[phenoxy(thiocarbonyl)]-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribo-pentofuranosyl]uracil

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Chemical Property of 1-[3-C-ethynyl-2-O-[phenoxy(thiocarbonyl)]-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribo-pentofuranosyl]uracil

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Technology Process of 1-[3-C-ethynyl-2-O-[phenoxy(thiocarbonyl)]-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribo-pentofuranosyl]uracil

There total 5 articles about 1-[3-C-ethynyl-2-O-[phenoxy(thiocarbonyl)]-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-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: 77.0%

: 1005-56-7
phenylcarbonochloridothioate

: 197297-97-5
1-[3-C-ethynyl-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribo-pentofuranosyl]uracil

: 197298-02-5
1-[3-C-ethynyl-2-O-[phenoxy(thiocarbonyl)]-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribo-pentofuranosyl]uracil

Guidance literature:: With dmap; In acetonitrile; for 2h;
DOI:10.1021/jo9704568

Reference yield:

: 90813-54-0
2',5'-bis-O-tert-butyldimethylsilyl-3'-ketouridine

: 197298-02-5
1-[3-C-ethynyl-2-O-[phenoxy(thiocarbonyl)]-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribo-pentofuranosyl]uracil

Guidance literature:: Multi-step reaction with 5 steps

1.1: CF₃COOH / H₂O / 0.5 h / 0 °C

2.1: BuLi / tetrahydrofuran; hexane / 1 h / -78 - -20 °C

2.2: CeCl₃ / tetrahydrofuran; hexane / 1 h / -78 °C

2.3: 0.74 g / tetrahydrofuran; hexane / 3 h / -78 °C

3.1: 82 percent / Bu₄NF / tetrahydrofuran / 0.5 h / 20 °C

4.1: 74 percent / pyridine; NEt(iPr)2

5.1: 77 percent / DMAP / acetonitrile / 2 h

With pyridine; dmap; n-butyllithium; tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; hexane; water; acetonitrile; 1.1: desilylation / 2.1: Metallation / 2.2: transmetallation / 2.3: Addition / 3.1: desilylation / 4.1: Cyclization / 5.1: Esterification;
DOI:10.1021/jo9704568

Reference yield:

: 162611-11-2
1-[2-O-(tert-butyldimethylsilyl)-β-D-erythro-pentofuran-3-ulosyl]uracil

: 197298-02-5
1-[3-C-ethynyl-2-O-[phenoxy(thiocarbonyl)]-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribo-pentofuranosyl]uracil

Guidance literature:: Multi-step reaction with 4 steps

1.1: BuLi / tetrahydrofuran; hexane / 1 h / -78 - -20 °C

1.2: CeCl₃ / tetrahydrofuran; hexane / 1 h / -78 °C

1.3: 0.74 g / tetrahydrofuran; hexane / 3 h / -78 °C

2.1: 82 percent / Bu₄NF / tetrahydrofuran / 0.5 h / 20 °C

3.1: 74 percent / pyridine; NEt(iPr)2

4.1: 77 percent / DMAP / acetonitrile / 2 h

With pyridine; dmap; n-butyllithium; tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; acetonitrile; 1.1: Metallation / 1.2: transmetallation / 1.3: Addition / 2.1: desilylation / 3.1: Cyclization / 4.1: Esterification;
DOI:10.1021/jo9704568