N⁶-benzoyl-9-((2R,3R,4R,5R)-4-(benzoxy)-5-{(1R)-2-(tert-butyldiphenylsilyl)oxy-1-[(imidazolethiocarbonyl)oxy]ethyl}-3-[(imidazolethiocarbonyl)oxy]tetrahydrofuran-2-yl)adenine

Base Information

• Chemical Name: N⁶-benzoyl-9-((2R,3R,4R,5R)-4-(benzoxy)-5-{(1R)-2-(tert-butyldiphenylsilyl)oxy-1-[(imidazolethiocarbonyl)oxy]ethyl}-3-[(imidazolethiocarbonyl)oxy]tetrahydrofuran-2-yl)adenine
• CAS No.: 184229-63-8
• Molecular Formula: C₄₉H₄₇N₉O₆S₂Si
• Molecular Weight: 950.186

Synonyms:N⁶-benzoyl-9-((2R,3R,4R,5R)-4-(benzoxy)-5-{(1R)-2-(tert-butyldiphenylsilyl)oxy-1-[(imidazolethiocarbonyl)oxy]ethyl}-3-[(imidazolethiocarbonyl)oxy]tetrahydrofuran-2-yl)adenine

Chemical Property of N⁶-benzoyl-9-((2R,3R,4R,5R)-4-(benzoxy)-5-{(1R)-2-(tert-butyldiphenylsilyl)oxy-1-[(imidazolethiocarbonyl)oxy]ethyl}-3-[(imidazolethiocarbonyl)oxy]tetrahydrofuran-2-yl)adenine

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Technology Process of N⁶-benzoyl-9-((2R,3R,4R,5R)-4-(benzoxy)-5-{(1R)-2-(tert-butyldiphenylsilyl)oxy-1-[(imidazolethiocarbonyl)oxy]ethyl}-3-[(imidazolethiocarbonyl)oxy]tetrahydrofuran-2-yl)adenine

There total 7 articles about N⁶-benzoyl-9-((2R,3R,4R,5R)-4-(benzoxy)-5-{(1R)-2-(tert-butyldiphenylsilyl)oxy-1-[(imidazolethiocarbonyl)oxy]ethyl}-3-[(imidazolethiocarbonyl)oxy]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: 90.0%

1,1'-Thiocarbonyldiimidazole (6160-65-2) + N-(9-{(2R,3R,4S,5R)-4-Benzyloxy-5-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-ethyl]-3-hydroxy-tetrahydro-furan-2-yl}-9H-purin-6-yl)-benzamide (184229-62-7) → N6-benzoyl-9-((2R,3R,4R,5R)-4-(benzoxy)-5-{(1R)-2-(tert-butyldiphenylsilyl)oxy-1-[(imidazolethiocarbonyl)oxy]ethyl}-3-[(imidazolethiocarbonyl)oxy]tetrahydrofuran-2-yl)adenine (184229-63-8)

Guidance literature:

In tetrahydrofuran; at 65 ℃; for 12h;

DOI:10.1021/ja961788h

Reference yield:

(1,2:5,6)-di-O-isopropylidene-D-gulose (14686-89-6) → N6-benzoyl-9-((2R,3R,4R,5R)-4-(benzoxy)-5-{(1R)-2-(tert-butyldiphenylsilyl)oxy-1-[(imidazolethiocarbonyl)oxy]ethyl}-3-[(imidazolethiocarbonyl)oxy]tetrahydrofuran-2-yl)adenine (184229-63-8)

Guidance literature:

Multi-step reaction with 6 steps

1: sodium hydride / dimethylformamide / 1 h / Ambient temperature

2: acetic acid, p-toluenesulfonic acid monohydrate / 1 h / Heating

3: 71 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 12 h / 55 °C

4: 86 percent / ethanolic NaOH / pyridine / 0.17 h / Ambient temperature

5: 97 percent / imidazole / CH₂Cl₂ / 1 h / Ambient temperature

6: 90 percent / tetrahydrofuran / 12 h / 65 °C

With 1H-imidazole; sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; sodium hydride; toluene-4-sulfonic acid; acetic acid; In tetrahydrofuran; pyridine; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja961788h

Reference yield:

1,2:5,6-di-O-isopropylidene-3-O-benzyl-α-D-allofuranose (22331-21-1) → N6-benzoyl-9-((2R,3R,4R,5R)-4-(benzoxy)-5-{(1R)-2-(tert-butyldiphenylsilyl)oxy-1-[(imidazolethiocarbonyl)oxy]ethyl}-3-[(imidazolethiocarbonyl)oxy]tetrahydrofuran-2-yl)adenine (184229-63-8)

Guidance literature:

Multi-step reaction with 5 steps

1: acetic acid, p-toluenesulfonic acid monohydrate / 1 h / Heating

2: 71 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 12 h / 55 °C

3: 86 percent / ethanolic NaOH / pyridine / 0.17 h / Ambient temperature

4: 97 percent / imidazole / CH₂Cl₂ / 1 h / Ambient temperature

5: 90 percent / tetrahydrofuran / 12 h / 65 °C

With 1H-imidazole; sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; toluene-4-sulfonic acid; acetic acid; In tetrahydrofuran; pyridine; dichloromethane; acetonitrile;

DOI:10.1021/ja961788h

upstream raw materials:

1,1'-Thiocarbonyldiimidazole

N-(9-{(2R,3R,4S,5R)-4-Benzyloxy-5-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-ethyl]-3-hydroxy-tetrahydro-furan-2-yl}-9H-purin-6-yl)-benzamide

(1,2:5,6)-di-O-isopropylidene-D-gulose

1,2:5,6-di-O-isopropylidene-3-O-benzyl-α-D-allofuranose

Downstream raw materials:

N-[9-((2R,4S,5R)-5-{2-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-ethyl}-4-hydroxy-tetrahydro-furan-2-yl)-9H-purin-6-yl]-benzamide

N-{9-[(2R,4S,5R)-4-Benzyloxy-5-(2-hydroxy-ethyl)-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide

N-{9-[(2R,4S,5R)-4-Hydroxy-5-(2-hydroxy-ethyl)-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide

N-(9-{(2R,4S,5R)-4-Benzyloxy-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-furan-2-yl}-9H-purin-6-yl)-benzamide

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