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

Base Information

• Chemical Name: N⁶-benzoyl-9-<(2S,4R,5R)-4-<(benzoyloxy)methyl>-5-(2-hydroxyethyl)tetrahydrofuran-2-yl>adenine
• CAS No.: 129399-16-2
• Molecular Formula: C₂₆H₂₅N₅O₅
• Molecular Weight: 487.515

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 16 articles about N⁶-benzoyl-9-<(2S,4R,5R)-4-<(benzoyloxy)methyl>-5-(2-hydroxyethyl)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:

(2RS,4R,5R)-2-methoxy-4-<(4-pivaloyloxy)methyl>-5-(2-hydroxyethyl)-tetrahydrofuran (128435-09-6,134056-11-4,134056-26-1) → N6-benzoyl-9-<(2S,4R,5R)-4-<(benzoyloxy)methyl>-5-(2-hydroxyethyl)tetrahydrofuran-2-yl>adenine (129399-16-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 84 percent / acidic cation-exchange resin (Dowex 50 W₈) / toluene / 5 h / Heating

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

3: 93 percent / pyridine / 0.5 h / Ambient temperature

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

With pyridine; sodium hydroxide; acidic cation-exchange resin (Dowex 50 W₈); N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; methanol; water; toluene;

DOI:10.1021/jo00012a018

Reference yield:

(1R,5R,6R)-6-<(pivaloyloxy)methyl>-2,8-dioxabicyclo-<3.2.1>octane (129518-74-7) → N6-benzoyl-9-<(2S,4R,5R)-4-<(benzoyloxy)methyl>-5-(2-hydroxyethyl)tetrahydrofuran-2-yl>adenine (129399-16-2)

Guidance literature:

Multi-step reaction with 3 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

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

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) → N6-benzoyl-9-<(2S,4R,5R)-4-<(benzoyloxy)methyl>-5-(2-hydroxyethyl)tetrahydrofuran-2-yl>adenine (129399-16-2)

Guidance literature:

Multi-step reaction with 10 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) MSTFA / 2) TMSOTf / 1) acetonitrile, r. t., 10 min, 2a) acetonitrile, r. t., 10 min, b) 40 deg C, 30 min

With pyridine; 2,2'-azobis(isobutyronitrile); dimethylsulfide borane complex; acidic cation-exchange resin (Dowex 50 W₈); N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide; sulfuric acid; dihydrogen peroxide; tri-n-butyl-tin hydride; sodium hydrogencarbonate; sodium iodide; dmap; trimethylsilyl trifluoromethanesulfonate; In methanol; chloroform; toluene; butanone;

DOI:10.1021/jo00012a018

upstream raw materials:

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

N-benzoyladenine

((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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