N⁶-benzoyl-9-<(2R,4R,5R)-4-<(benzoyloxy)methyl>-5-<2-(acetylthio)ethyl>tetrahydrofuran-2-yl>adenine

Base Information

• Chemical Name: N⁶-benzoyl-9-<(2R,4R,5R)-4-<(benzoyloxy)methyl>-5-<2-(acetylthio)ethyl>tetrahydrofuran-2-yl>adenine
• CAS No.: 129399-04-8
• Molecular Formula: C₂₈H₂₇N₅O₅S
• Molecular Weight: 545.619

Synonyms:N⁶-benzoyl-9-<(2R,4R,5R)-4-<(benzoyloxy)methyl>-5-<2-(acetylthio)ethyl>tetrahydrofuran-2-yl>adenine

Chemical Property of N⁶-benzoyl-9-<(2R,4R,5R)-4-<(benzoyloxy)methyl>-5-<2-(acetylthio)ethyl>tetrahydrofuran-2-yl>adenine

Chemical Property:

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Technology Process of N⁶-benzoyl-9-<(2R,4R,5R)-4-<(benzoyloxy)methyl>-5-<2-(acetylthio)ethyl>tetrahydrofuran-2-yl>adenine

There total 17 articles about N⁶-benzoyl-9-<(2R,4R,5R)-4-<(benzoyloxy)methyl>-5-<2-(acetylthio)ethyl>tetrahydrofuran-2-yl>adenine 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: 69.0%

N6-benzoyl-9-<(2R,4R,5R)-4-<(benzoyloxy)methyl>-5-(2-hydroxyethyl)tetrahydrofuran-2-yl>adenine (129399-09-3) + tiolacetic acid (507-09-5) → N6-benzoyl-9-<(2R,4R,5R)-4-<(benzoyloxy)methyl>-5-<2-(acetylthio)ethyl>tetrahydrofuran-2-yl>adenine (129399-04-8)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 ℃;

DOI:10.1016/S0040-4039(00)94548-9

Reference yield:

(1R,5R,6R)-6-<(pivaloyloxy)methyl>-2,8-dioxabicyclo-<3.2.1>octane (129518-74-7) → N6-benzoyl-9-<(2R,4R,5R)-4-<(benzoyloxy)methyl>-5-<2-(acetylthio)ethyl>tetrahydrofuran-2-yl>adenine (129399-04-8)

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) MSTFA / 2) TMSOTf / 1) acetonitrile, r. t., 10 min, 2a) acetonitrile, r. t., 10 min, b) 40 deg C, 30 min

4: 69 percent / Ph₃P, diisopropyl azodicarboxylate / tetrahydrofuran / 0.5 h / 0 °C

With pyridine; sodium hydroxide; di-isopropyl azodicarboxylate; N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide; triphenylphosphine; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; methanol; water;

DOI:10.1021/jo00012a018

Reference yield:

(1R,5R,6R)-6-<(benzoyloxy)methyl>-2,8-dioxabicyclo-<3.2.1>octane (129399-08-2) → N6-benzoyl-9-<(2R,4R,5R)-4-<(benzoyloxy)methyl>-5-<2-(acetylthio)ethyl>tetrahydrofuran-2-yl>adenine (129399-04-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) MSTFA / 2) TMSOTf / 1) acetonitrile, r. t., 10 min, 2a) acetonitrile, r. t., 10 min, b) 40 deg C, 30 min

2: 69 percent / Ph₃P, diisopropyl azodicarboxylate / tetrahydrofuran / 0.5 h / 0 °C

With di-isopropyl azodicarboxylate; N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide; triphenylphosphine; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran;

DOI:10.1021/jo00012a018

upstream raw materials:

N⁶-benzoyl-9-<(2R,4R,5R)-4-<(benzoyloxy)methyl>-5-(2-hydroxyethyl)tetrahydrofuran-2-yl>adenine

tiolacetic acid

((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

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

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