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

Base Information

Chemical Name:1-<(2S,4R,5R)-4-<(benzoyloxy)methyl>-5-<2-(acetylthio)ethyl>tetrahydrofuran-2-yl>uracil
CAS No.:130881-29-7
Molecular Formula:C₂₀H₂₂N₂O₆S
Molecular Weight:418.47
Hs Code.:

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

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

Chemical Property:

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

There total 18 articles about 1-<(2S,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: 89.0%

: 129399-15-1
N²-isobutyryl-7-<(2β,4R,5R)-4-<(benzoyloxy)methyl>-5-2-(hydroxyethyl)tetrahydrofuran-2-yl>guanine

: 507-09-5
tiolacetic acid

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

: 129954-15-0
N²-isobutyryl-7-<(2R,4R,5R)-4-<(benzoyloxy)methyl>-5-<2-(acetylthio)ethyl>tetrahydrofuran-2-yl>guanine

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

Reference yield:

: 134056-12-5
(1R,5R,6R)-6-(hydroxymethyl)-2,8-dioxabicyclo-<3.2.1>octane

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

Guidance literature:: Multi-step reaction with 3 steps

1: 93 percent / pyridine / 0.5 h / Ambient temperature

2: 1) TMSCl, HMDS / 2) TMSOTf / 1) acetonitrile, r. t., 10 min, 2a) acetonitrile, r. t., 10 min, b) 40 deg C, 15 min

3: PPh₃, diisopropyl azodicarboxylate / tetrahydrofuran / 1 h / 0 °C

With pyridine; chloro-trimethyl-silane; di-isopropyl azodicarboxylate; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran;
DOI:10.1021/jo00012a018

Reference yield:

: 129518-74-7
(1R,5R,6R)-6-<(pivaloyloxy)methyl>-2,8-dioxabicyclo-<3.2.1>octane

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

Guidance literature:: Multi-step reaction with 4 steps

1: 90 percent / 10 M NaOH / methanol; H₂O; tetrahydrofuran / 2 h / Ambient temperature

2: 93 percent / pyridine / 0.5 h / Ambient temperature

3: 1) TMSCl, HMDS / 2) TMSOTf / 1) acetonitrile, r. t., 10 min, 2a) acetonitrile, r. t., 10 min, b) 40 deg C, 15 min

4: PPh₃, diisopropyl azodicarboxylate / tetrahydrofuran / 1 h / 0 °C

With pyridine; sodium hydroxide; chloro-trimethyl-silane; di-isopropyl azodicarboxylate; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; methanol; water;
DOI:10.1021/jo00012a018