1-[(1R,3S,5S,7R,8R)-5-(2-bromophenyl)-8-hydroxy-7-(hydroxymethyl)-2,6-dioxabicyclo[3.3.0]octan-3-yl]thymine

Base Information

Chemical Name:1-[(1R,3S,5S,7R,8R)-5-(2-bromophenyl)-8-hydroxy-7-(hydroxymethyl)-2,6-dioxabicyclo[3.3.0]octan-3-yl]thymine
CAS No.:881424-02-8
Molecular Formula:C₁₈H₁₉BrN₂O₆
Molecular Weight:439.263
Hs Code.:

Synonyms:1-[(1R,3S,5S,7R,8R)-5-(2-bromophenyl)-8-hydroxy-7-(hydroxymethyl)-2,6-dioxabicyclo[3.3.0]octan-3-yl]thymine

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Chemical Property of 1-[(1R,3S,5S,7R,8R)-5-(2-bromophenyl)-8-hydroxy-7-(hydroxymethyl)-2,6-dioxabicyclo[3.3.0]octan-3-yl]thymine

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Technology Process of 1-[(1R,3S,5S,7R,8R)-5-(2-bromophenyl)-8-hydroxy-7-(hydroxymethyl)-2,6-dioxabicyclo[3.3.0]octan-3-yl]thymine

There total 9 articles about 1-[(1R,3S,5S,7R,8R)-5-(2-bromophenyl)-8-hydroxy-7-(hydroxymethyl)-2,6-dioxabicyclo[3.3.0]octan-3-yl]thymine 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: 99.0%

: Acetic acid (2R,3R,3aR,5S,6aS)-6a-(2-bromo-phenyl)-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-hexahydro-furo[3,2-b]furan-3-yl ester

: 881424-02-8
1-[(1R,3S,5S,7R,8R)-5-(2-bromophenyl)-8-hydroxy-7-(hydroxymethyl)-2,6-dioxabicyclo[3.3.0]octan-3-yl]thymine

Guidance literature:: With sodium hydroxide; In tetrahydrofuran; methanol; water; at 0 ℃;
DOI:10.1021/jo052413u

Reference yield:

: 881423-76-3
1-(2-bromophenyl)-5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose

: 881424-02-8
1-[(1R,3S,5S,7R,8R)-5-(2-bromophenyl)-8-hydroxy-7-(hydroxymethyl)-2,6-dioxabicyclo[3.3.0]octan-3-yl]thymine

Guidance literature:: Multi-step reaction with 7 steps

1: ZnBr₂ / nitromethane / 0 - 20 °C

2: OsO₄; NaIO₄; pyridine / H₂O / 30 h / 20 °C

3: H₂SO₄ / tetrahydrofuran; H₂O / 12 h / 60 °C

4: 663 mg / pyridine / 0 - 20 °C

5: 62 percent / trimethylsilyl N-(trimethylsilyl)acetimidate; TMSOTf / acetonitrile / 1 h / 20 °C

6: TBAF / tetrahydrofuran / 20 °C

7: 99 percent / NaOH / tetrahydrofuran; methanol; H₂O / 0 °C

With pyridine; sodium hydroxide; sodium periodate; osmium(VIII) oxide; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; tetrabutyl ammonium fluoride; zinc dibromide; In tetrahydrofuran; methanol; nitromethane; water; acetonitrile;
DOI:10.1021/jo052413u

Reference yield:

: [4-(2-bromo-phenyl)-6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-acetaldehyde

: 881424-02-8
1-[(1R,3S,5S,7R,8R)-5-(2-bromophenyl)-8-hydroxy-7-(hydroxymethyl)-2,6-dioxabicyclo[3.3.0]octan-3-yl]thymine

Guidance literature:: Multi-step reaction with 5 steps

1: H₂SO₄ / tetrahydrofuran; H₂O / 12 h / 60 °C

2: 663 mg / pyridine / 0 - 20 °C

3: 62 percent / trimethylsilyl N-(trimethylsilyl)acetimidate; TMSOTf / acetonitrile / 1 h / 20 °C

4: TBAF / tetrahydrofuran / 20 °C

5: 99 percent / NaOH / tetrahydrofuran; methanol; H₂O / 0 °C

With pyridine; sodium hydroxide; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; tetrabutyl ammonium fluoride; In tetrahydrofuran; methanol; water; acetonitrile;
DOI:10.1021/jo052413u