N⁶-benzoyl-8-{[(tert-butyl)diphenylsilyloxy]methyl}-2',3'-O-isopropylideneadenosine

Base Information

• Chemical Name: N⁶-benzoyl-8-{[(tert-butyl)diphenylsilyloxy]methyl}-2',3'-O-isopropylideneadenosine
• CAS No.: 928034-65-5
• Molecular Formula: C₃₇H₄₁N₅O₆Si
• Molecular Weight: 679.848

Synonyms:N⁶-benzoyl-8-{[(tert-butyl)diphenylsilyloxy]methyl}-2',3'-O-isopropylideneadenosine

Chemical Property of N⁶-benzoyl-8-{[(tert-butyl)diphenylsilyloxy]methyl}-2',3'-O-isopropylideneadenosine

Chemical Property:

Purity/Quality:

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Technology Process of N⁶-benzoyl-8-{[(tert-butyl)diphenylsilyloxy]methyl}-2',3'-O-isopropylideneadenosine

There total 4 articles about N⁶-benzoyl-8-{[(tert-butyl)diphenylsilyloxy]methyl}-2',3'-O-isopropylideneadenosine 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: 79.0%

N6-benzoyl-5'-O-[(tert-butyl)dimethylsilyl]-8-{[(tert-butyl)diphenylsilyloxy]methyl}-2',3'-O-isopropylideneadenosine (928034-64-4) → N6-benzoyl-8-{[(tert-butyl)diphenylsilyloxy]methyl}-2',3'-O-isopropylideneadenosine (928034-65-5)

Guidance literature:

With fluorosilicic acid; In water; acetonitrile; tert-butyl alcohol; at 27 ℃; for 12h;

DOI:10.1002/hlca.200690259

Reference yield:

N6-benzoyl-5'-O-[(tert-butyl)dimethylsilyl]-8-(hydroxymethyl)-2',3'-O-isopropylideneadenosine (928034-63-3) → N6-benzoyl-8-{[(tert-butyl)diphenylsilyloxy]methyl}-2',3'-O-isopropylideneadenosine (928034-65-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / 1H-imidazole; DMAP / CH₂Cl₂ / 9 h / 27 °C

2: 79 percent / H₂SiF₆ / acetonitrile; H₂O; 2-methyl-propan-2-ol / 12 h / 27 °C

With 1H-imidazole; dmap; fluorosilicic acid; In dichloromethane; water; acetonitrile; tert-butyl alcohol;

DOI:10.1002/hlca.200690259

Reference yield:

N-6-benzoyl-2',3'-O-isopropylideneadenosine (39947-04-1) → N6-benzoyl-8-{[(tert-butyl)diphenylsilyloxy]methyl}-2',3'-O-isopropylideneadenosine (928034-65-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 88 percent / 1H-imidazole; DMAP / CH₂Cl₂ / 5 h / 25 °C

2.1: (i-Pr)2NH; BuLi / hexane; tetrahydrofuran / 3 h / -76 °C

2.2: hexane; tetrahydrofuran / 3 h / -76 °C

2.3: 83 percent / NaBH₄ / ethanol; hexane; tetrahydrofuran / 3 h / 27 °C

3.1: 89 percent / 1H-imidazole; DMAP / CH₂Cl₂ / 9 h / 27 °C

4.1: 79 percent / H₂SiF₆ / acetonitrile; H₂O; 2-methyl-propan-2-ol / 12 h / 27 °C

With 1H-imidazole; dmap; n-butyllithium; fluorosilicic acid; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; water; acetonitrile; tert-butyl alcohol;

DOI:10.1002/hlca.200690259

upstream raw materials:

N⁶-benzoyl-5'-O-[(tert-butyl)dimethylsilyl]-8-{[(tert-butyl)diphenylsilyloxy]methyl}-2',3'-O-isopropylideneadenosine

N⁶-benzoyl-5'-O-[(tert-butyl)dimethylsilyl]-8-(hydroxymethyl)-2',3'-O-isopropylideneadenosine

N-6-benzoyl-2',3'-O-isopropylideneadenosine

N⁶-benzoyl-5'-O-[(tert-butyl)dimethylsilyl]-2',3'-O-isopropylideneadenosine

Downstream raw materials:

N-[8-(tert-butyl-diphenyl-silanyloxymethyl)-9-(6-formyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl]-benzamide

8-{[(tert-butyl)diphenylsilyloxy]methyl}-9-[6,7-dideoxy-2,3-O-isopropylidene-β-D-allo-hept-6-ynofuranosyl]adenine

8-{[(tert-butyl)diphenylsilyloxy]methyl}-9-[6,7-dideoxy-2,3-O-isopropylidene-α-L-talo-hept-6-ynofuranosyl]adenine

N⁶-benzoyl-8-{[(tert-butyl)diphenylsilyloxy]methyl}-9-[6,7-dideoxy-2,3-O-isopropylidene-7-C-(trimethylsilyl)-β-D-allo-hept-6-ynofuranosyl]adenine

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