N⁶-benzoyl-9-{(2R,3R,4R,5R)-4-benzoyloxymethyl-5-(2-hydroxyethyl)-3-[(m-trifluoromethyl)benzoyloxy]tetrahydrofuran-2-yl}adenine

Base Information

• Chemical Name: N⁶-benzoyl-9-{(2R,3R,4R,5R)-4-benzoyloxymethyl-5-(2-hydroxyethyl)-3-[(m-trifluoromethyl)benzoyloxy]tetrahydrofuran-2-yl}adenine
• CAS No.: 441044-22-0
• Molecular Formula: C₃₄H₂₈F₃N₅O₇
• Molecular Weight: 675.621

Synonyms:N⁶-benzoyl-9-{(2R,3R,4R,5R)-4-benzoyloxymethyl-5-(2-hydroxyethyl)-3-[(m-trifluoromethyl)benzoyloxy]tetrahydrofuran-2-yl}adenine

Chemical Property of N⁶-benzoyl-9-{(2R,3R,4R,5R)-4-benzoyloxymethyl-5-(2-hydroxyethyl)-3-[(m-trifluoromethyl)benzoyloxy]tetrahydrofuran-2-yl}adenine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N⁶-benzoyl-9-{(2R,3R,4R,5R)-4-benzoyloxymethyl-5-(2-hydroxyethyl)-3-[(m-trifluoromethyl)benzoyloxy]tetrahydrofuran-2-yl}adenine

There total 2 articles about N⁶-benzoyl-9-{(2R,3R,4R,5R)-4-benzoyloxymethyl-5-(2-hydroxyethyl)-3-[(m-trifluoromethyl)benzoyloxy]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: 67.0%

(1R,5R,6R,7R)-6-<(benzoyloxy)methyl>-7-<<3-(trifluoromethyl)benzoyl>oxy>-2,8-dioxabicyclo<3.2.1>octane (134056-17-0) + N-benzoyladenine (4005-49-6) → N6-benzoyl-9-{(2R,3R,4R,5R)-4-benzoyloxymethyl-5-(2-hydroxyethyl)-3-[(m-trifluoromethyl)benzoyloxy]tetrahydrofuran-2-yl}adenine (441044-22-0)

Guidance literature:

(1R,5R,6R,7R)-6-<(benzoyloxy)methyl>-7-<<3-(trifluoromethyl)benzoyl>oxy>-2,8-dioxabicyclo<3.2.1>octane; N-benzoyladenine; With N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide; In acetonitrile; at 20 ℃; for 0.25h;

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 60 ℃; for 45h; Further stages.;

DOI:10.1021/jo0003910

Reference yield: 42.0%

(1R,5R,6R,7R)-6-<(benzoyloxy)methyl>-7-<<3-(trifluoromethyl)benzoyl>oxy>-2,8-dioxabicyclo<3.2.1>octane (134056-17-0) + N-benzoyladenine (4005-49-6) → N6-benzoyl-9-{(2R,3R,4R,5R)-4-benzoyloxymethyl-5-(2-hydroxyethyl)-3-[(m-trifluoromethyl)benzoyloxy]tetrahydrofuran-2-yl}adenine (441044-22-0) + N6-benzoyl-7-{(2R,3R,4R,5R)-4-benzoyloxymethyl-5-(2-hydroxyethyl)-3-[(m-trifluoromethyl)benzoyloxy]tetrahydrofuran-2-yl}adenine

Guidance literature:

(1R,5R,6R,7R)-6-<(benzoyloxy)methyl>-7-<<3-(trifluoromethyl)benzoyl>oxy>-2,8-dioxabicyclo<3.2.1>octane; N-benzoyladenine; With N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide; In acetonitrile; at 20 ℃; for 0.25h;

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 20 ℃; for 20h; Further stages.;

DOI:10.1021/jo0003910

Reference yield:

N6-benzoyl-9-{(2R,3R,4R,5R)-4-benzoyloxymethyl-5-(2-hydroxyethyl)-3-[(m-trifluoromethyl)benzoyloxy]tetrahydrofuran-2-yl}adenine (441044-22-0) → Thioacetic acid S-((2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-{2-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-ethyl}-tetrahydro-furan-3-ylmethyl) ester

Guidance literature:

Multi-step reaction with 5 steps

1: triethylamine / tetrahydrofuran

2: 52 percent / NaOH / H₂O

3: Ph₃P; diisopropyl azodicarboxylate / tetrahydrofuran

4: Bu₃SnH; azobisisobutyronitrile

With sodium hydroxide; 2,2'-azobis(isobutyronitrile); di-isopropyl azodicarboxylate; tri-n-butyl-tin hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; water; 3: Mitsunobu reaction / 5: Barton deoxygenation;

DOI:10.1021/jo0003910

upstream raw materials:

(1R,5R,6R,7R)-6-<(benzoyloxy)methyl>-7-<<3-(trifluoromethyl)benzoyl>oxy>-2,8-dioxabicyclo<3.2.1>octane

N-benzoyladenine

Downstream raw materials:

3-Trifluoromethyl-benzoic acid (2R,3R,4R,5R)-2-(6-benzoylamino-purin-9-yl)-4-benzoyloxymethyl-5-{2-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-ethyl}-tetrahydro-furan-3-yl ester

N-[9-(5-{2-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-ethyl}-3-hydroxy-4-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-benzamide

Thioacetic acid S-((2R,3S,4R,5R)-5-(6-benzoylamino-purin-9-yl)-2-{2-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-ethyl}-4-hydroxy-tetrahydro-furan-3-ylmethyl) ester

Benzoic acid (2R,3S,4R,5R)-5-(6-benzoylamino-purin-9-yl)-2-{2-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-ethyl}-4-hydroxy-tetrahydro-furan-3-ylmethyl ester

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