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

Base Information

• Chemical Name: N²-isobutyryl-7-<(2R,4R,5R)-4-<(benzoyloxy)methyl>-5-<2-(acetylthio)ethyl>tetrahydrofuran-2-yl>guanine
• CAS No.: 129954-15-0
• Molecular Formula: C₂₅H₂₉N₅O₆S
• Molecular Weight: 527.601

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

Chemical Property of N²-isobutyryl-7-<(2R,4R,5R)-4-<(benzoyloxy)methyl>-5-<2-(acetylthio)ethyl>tetrahydrofuran-2-yl>guanine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N²-isobutyryl-7-<(2R,4R,5R)-4-<(benzoyloxy)methyl>-5-<2-(acetylthio)ethyl>tetrahydrofuran-2-yl>guanine

There total 16 articles about N²-isobutyryl-7-<(2R,4R,5R)-4-<(benzoyloxy)methyl>-5-<2-(acetylthio)ethyl>tetrahydrofuran-2-yl>guanine 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%

N2-isobutyryl-7-<(2β,4R,5R)-4-<(benzoyloxy)methyl>-5-2-(hydroxyethyl)tetrahydrofuran-2-yl>guanine (129399-15-1) + tiolacetic acid (507-09-5) → 1-<(2S,4R,5R)-4-<(benzoyloxy)methyl>-5-<2-(acetylthio)ethyl>tetrahydrofuran-2-yl>uracil (130881-29-7) + N2-isobutyryl-7-<(2R,4R,5R)-4-<(benzoyloxy)methyl>-5-<2-(acetylthio)ethyl>tetrahydrofuran-2-yl>guanine (129954-15-0)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1021/jo00012a018

Reference yield:

((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 (69832-48-0) → N2-isobutyryl-7-<(2R,4R,5R)-4-<(benzoyloxy)methyl>-5-<2-(acetylthio)ethyl>tetrahydrofuran-2-yl>guanine (129954-15-0)

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: 66 percent / Bu₃SnH, azoisobutyronitrile / toluene / 1 h / 75 °C

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

11: 89 percent / PPh₃, diisopropyl azodicarboxylate / tetrahydrofuran / 1 h / 0 °C

With pyridine; chloro-trimethyl-silane; 2,2'-azobis(isobutyronitrile); di-isopropyl azodicarboxylate; dimethylsulfide borane complex; acidic cation-exchange resin (Dowex 50 W₈); sulfuric acid; dihydrogen peroxide; tri-n-butyl-tin hydride; sodium hydrogencarbonate; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; sodium iodide; dmap; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; methanol; chloroform; toluene; butanone;

DOI:10.1021/jo00012a018

Reference yield:

(1R,5R,6R)-6-<(pivaloyloxy)methyl>-2,8-dioxabicyclo-<3.2.1>octane (129518-74-7) → N2-isobutyryl-7-<(2R,4R,5R)-4-<(benzoyloxy)methyl>-5-<2-(acetylthio)ethyl>tetrahydrofuran-2-yl>guanine (129954-15-0)

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: 89 percent / 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

upstream raw materials:

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

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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