Acetic acid (2R,3R,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-3-(6-diphenylacetylamino-purin-9-yl)-propoxy]-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-3-(6-diphenylacetylamino-purin-9-yl)-propoxy]-tetrahydro-pyran-4-yl ester
• CAS No.: 190968-22-0
• Molecular Formula: C₅₇H₆₁N₅O₁₁Si
• Molecular Weight: 1020.22

Synonyms:Acetic acid (2R,3R,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-3-(6-diphenylacetylamino-purin-9-yl)-propoxy]-tetrahydro-pyran-4-yl ester

Chemical Property of Acetic acid (2R,3R,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-3-(6-diphenylacetylamino-purin-9-yl)-propoxy]-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of Acetic acid (2R,3R,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-3-(6-diphenylacetylamino-purin-9-yl)-propoxy]-tetrahydro-pyran-4-yl ester

There total 7 articles about Acetic acid (2R,3R,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-3-(6-diphenylacetylamino-purin-9-yl)-propoxy]-tetrahydro-pyran-4-yl ester 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: 80.0%

3,4,6-tri-O-acetyl-2-O-benzyl-α/β-D-glucopyranosyl trichloroacetimidate + N-{9-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-propyl]-9H-purin-6-yl}-2,2-diphenyl-acetamide (190968-20-8) → Acetic acid (2R,3R,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-3-(6-diphenylacetylamino-purin-9-yl)-propoxy]-tetrahydro-pyran-4-yl ester (190968-22-0)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; for 0.166667h; Ambient temperature;

DOI:10.1016/S0040-4020(97)00308-6

Reference yield:

diphenylacetic anhydride (1760-46-9) → Acetic acid (2R,3R,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-3-(6-diphenylacetylamino-purin-9-yl)-propoxy]-tetrahydro-pyran-4-yl ester (190968-22-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 82 percent / pyridine / 16 h / 50 °C

2: aq. AcOH / 60 °C

3: pyridine / 2 h / Ambient temperature

4: 71 percent / imidazole / toluene / 16 h / 60 °C

5: 86 percent / pyrrole, TFA / CH₂Cl₂ / 0.17 h / Ambient temperature

6: 80 percent / TMSOTf / CH₂Cl₂ / 0.17 h / Ambient temperature

With pyridine; 1H-imidazole; pyrrole; trimethylsilyl trifluoromethanesulfonate; acetic acid; trifluoroacetic acid; In dichloromethane; toluene;

DOI:10.1016/S0040-4020(97)00308-6

Reference yield:

(S)-9-(1,2-isopropylidenedioxyprop-3-yl)-adenine (54262-84-9) → Acetic acid (2R,3R,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-3-(6-diphenylacetylamino-purin-9-yl)-propoxy]-tetrahydro-pyran-4-yl ester (190968-22-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 82 percent / pyridine / 16 h / 50 °C

2: aq. AcOH / 60 °C

3: pyridine / 2 h / Ambient temperature

4: 71 percent / imidazole / toluene / 16 h / 60 °C

5: 86 percent / pyrrole, TFA / CH₂Cl₂ / 0.17 h / Ambient temperature

6: 80 percent / TMSOTf / CH₂Cl₂ / 0.17 h / Ambient temperature

With pyridine; 1H-imidazole; pyrrole; trimethylsilyl trifluoromethanesulfonate; acetic acid; trifluoroacetic acid; In dichloromethane; toluene;

DOI:10.1016/S0040-4020(97)00308-6

upstream raw materials:

N-{9-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-propyl]-9H-purin-6-yl}-2,2-diphenyl-acetamide

diphenylacetic anhydride

(S)-9-(1,2-isopropylidenedioxyprop-3-yl)-adenine

N-[9-((S)-2,3-Dihydroxy-propyl)-9H-purin-6-yl]-2,2-diphenyl-acetamide

Downstream raw materials:

N-{9-[(S)-3-((2S,3R,4S,5S,6R)-3-Benzyloxy-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-hydroxy-propyl]-9H-purin-6-yl}-2,2-diphenyl-acetamide

N-[9-((S)-3-{(2S,3R,4S,5S,6R)-3-Benzyloxy-6-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4,5-dihydroxy-tetrahydro-pyran-2-yloxy}-2-hydroxy-propyl)-9H-purin-6-yl]-2,2-diphenyl-acetamide

Acetic acid (2R,3R,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-[(S)-3-(6-diphenylacetylamino-purin-9-yl)-2-hydroxy-propoxy]-tetrahydro-pyran-4-yl ester

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