1-[(1S)-2,3,5-tri-O-acetyl-1α-phenylseleno-β-D-ribo-pentafuranosyl]uracil

Base Information

Chemical Name:1-[(1S)-2,3,5-tri-O-acetyl-1α-phenylseleno-β-D-ribo-pentafuranosyl]uracil
CAS No.:914294-88-5
Molecular Formula:C₂₁H₂₂N₂O₉Se
Molecular Weight:525.374
Hs Code.:

Synonyms:1-[(1S)-2,3,5-tri-O-acetyl-1α-phenylseleno-β-D-ribo-pentafuranosyl]uracil

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Chemical Property of 1-[(1S)-2,3,5-tri-O-acetyl-1α-phenylseleno-β-D-ribo-pentafuranosyl]uracil

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Technology Process of 1-[(1S)-2,3,5-tri-O-acetyl-1α-phenylseleno-β-D-ribo-pentafuranosyl]uracil

There total 3 articles about 1-[(1S)-2,3,5-tri-O-acetyl-1α-phenylseleno-β-D-ribo-pentafuranosyl]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: 91.0%

: Acetic acid (2S,3R,4R,5R)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-5-hydroxymethyl-2-phenylselanyl-tetrahydro-furan-3-yl ester

: 108-24-7
acetic anhydride

: 914294-88-5
1-[(1S)-2,3,5-tri-O-acetyl-1α-phenylseleno-β-D-ribo-pentafuranosyl]uracil

Guidance literature:: With dmap; triethylamine; In acetonitrile; at 20 ℃; for 0.5h;
DOI:10.1016/j.tet.2006.07.101

Reference yield:

: Acetic acid (2S,3R,3aR,9aR)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5,5,7,7-tetraisopropyl-2-phenylselanyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl ester

: 914294-88-5
1-[(1S)-2,3,5-tri-O-acetyl-1α-phenylseleno-β-D-ribo-pentafuranosyl]uracil

Guidance literature:: Multi-step reaction with 2 steps

1: TBAF; AcOH / tetrahydrofuran / 1 h / 0 °C

2: 91 percent / 4-(dimethylamino)pyridine; triethylamine / acetonitrile / 0.5 h / 20 °C

With dmap; tetrabutyl ammonium fluoride; acetic acid; triethylamine; In tetrahydrofuran; acetonitrile;
DOI:10.1016/j.tet.2006.07.101

Reference yield:

: 288103-33-3
1-[1-C-Phenylseleno-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribo-pentofuranosyl]uracil

: 914294-88-5
1-[(1S)-2,3,5-tri-O-acetyl-1α-phenylseleno-β-D-ribo-pentafuranosyl]uracil

Guidance literature:: Multi-step reaction with 3 steps

1: 4-(dimethylamino)pyridine; triethylamine / acetonitrile / 1 h / 20 °C

2: TBAF; AcOH / tetrahydrofuran / 1 h / 0 °C

3: 91 percent / 4-(dimethylamino)pyridine; triethylamine / acetonitrile / 0.5 h / 20 °C

With dmap; tetrabutyl ammonium fluoride; acetic acid; triethylamine; In tetrahydrofuran; acetonitrile;
DOI:10.1016/j.tet.2006.07.101