1-<(2R,4R,5R)-4-<(benzoyloxy)methyl>-5-<2-(acetylthio)ethyl>tetrahydrofuran-2-yl>uracil

Base Information

Chemical Name:1-<(2R,4R,5R)-4-<(benzoyloxy)methyl>-5-<2-(acetylthio)ethyl>tetrahydrofuran-2-yl>uracil
CAS No.:129399-06-0
Molecular Formula:C₂₀H₂₂N₂O₆S
Molecular Weight:418.47
Hs Code.:

Synonyms:1-<(2R,4R,5R)-4-<(benzoyloxy)methyl>-5-<2-(acetylthio)ethyl>tetrahydrofuran-2-yl>uracil

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Chemical Property of 1-<(2R,4R,5R)-4-<(benzoyloxy)methyl>-5-<2-(acetylthio)ethyl>tetrahydrofuran-2-yl>uracil

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Technology Process of 1-<(2R,4R,5R)-4-<(benzoyloxy)methyl>-5-<2-(acetylthio)ethyl>tetrahydrofuran-2-yl>uracil

There total 18 articles about 1-<(2R,4R,5R)-4-<(benzoyloxy)methyl>-5-<2-(acetylthio)ethyl>tetrahydrofuran-2-yl>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: 67.0%

: 129399-14-0
1-<(2R,4R,5R)-4-<(benzoyloxy)methyl>-5-(2-hydroxyethyl)tetrahydrofuran-2-yl>uracil

: 507-09-5
tiolacetic acid

: 129399-06-0
1-<(2R,4R,5R)-4-<(benzoyloxy)methyl>-5-<2-(acetylthio)ethyl>tetrahydrofuran-2-yl>uracil

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 ℃; for 1h;
DOI:10.1021/jo00012a018

Reference yield:

: 129399-14-0,129399-20-8
1-<(2RS,4R,5R)-4-<(benzoyloxy)methyl>-5-(2-hydroxyethyl)tetrahydrofuran-2-yl>uracil

: 507-09-5
tiolacetic acid

: 129399-06-0
1-<(2R,4R,5R)-4-<(benzoyloxy)methyl>-5-<2-(acetylthio)ethyl>tetrahydrofuran-2-yl>uracil

: 130881-29-7
1-<(2S,4R,5R)-4-<(benzoyloxy)methyl>-5-<2-(acetylthio)ethyl>tetrahydrofuran-2-yl>uracil

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 ℃; Yield given;
DOI:10.1016/S0040-4039(00)94548-9

Reference yield:

: 69832-48-0
((3aR,5S,6R,6aR)-tetrahydro-2,2-dimethyl-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)furo[2,3-d][1,3]dioxol-6-yl)methanol

: 129399-06-0
1-<(2R,4R,5R)-4-<(benzoyloxy)methyl>-5-<2-(acetylthio)ethyl>tetrahydrofuran-2-yl>uracil

Guidance literature:: Multi-step reaction with 11 steps

1: pyridine / DMAP / 23 h / Ambient temperature

2: 1.6percent H₂SO₄ / methanol; CHCl₃ / 84 h

3: pyridine / 2 h / Ambient temperature

4: NaI / butan-2-one / 15 h / Heating

5: 1) BH₃*Me₂S, 2) NaHCO₃, 30percent H₂O₂ / 1a) THF, 0-4 deg C, 24 h, b) THF, methanol, 0 deg C, 1 h, 2) THF, methanol, water, up to r. t., 2 h

6: acidic cation-exchange resin (Dowex 50 W₈) / methanol / 5.5 h / Heating

7: acidic cation-exchange resin (Dowex 50 W₈) / toluene / 0.25 h / Heating

8: 88 percent / pyridine / DMAP / 3 h / Ambient temperature

9: 1) MSTFA / 2) SnCl₄ / 1) acetonitrile, 80 deg C, 30 min, 2) acetonitrile, r. t., 40 h

10: 85 percent / N-methylcarbazole / H₂O; propan-2-ol / 1.5 h / 10 °C / Irradiation

11: 67 percent / Ph₃P, diisopropyl azodicarboxylate / tetrahydrofuran / 1 h / 0 °C

With pyridine; N-methylcarbazole; di-isopropyl azodicarboxylate; dimethylsulfide borane complex; acidic cation-exchange resin (Dowex 50 W₈); N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide; sulfuric acid; dihydrogen peroxide; sodium hydrogencarbonate; triphenylphosphine; sodium iodide; dmap; tin(IV) chloride; In tetrahydrofuran; methanol; chloroform; water; isopropyl alcohol; toluene; butanone;
DOI:10.1021/jo00012a018