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

Base Information

• Chemical Name: N⁶-benzoyl-5'-O-[(tert-butyl)dimethylsilyl]-8-{[(tert-butyl)diphenylsilyloxy]methyl}-2',3'-O-isopropylideneadenosine
• CAS No.: 928034-64-4
• Molecular Formula: C₄₃H₅₅N₅O₆Si₂
• Molecular Weight: 794.111

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

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

Chemical Property:

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

There total 4 articles about N⁶-benzoyl-5'-O-[(tert-butyl)dimethylsilyl]-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: 89.0%

N6-benzoyl-5'-O-[(tert-butyl)dimethylsilyl]-8-(hydroxymethyl)-2',3'-O-isopropylideneadenosine (928034-63-3) + tert-butylchlorodiphenylsilane (58479-61-1) → N6-benzoyl-5'-O-[(tert-butyl)dimethylsilyl]-8-{[(tert-butyl)diphenylsilyloxy]methyl}-2',3'-O-isopropylideneadenosine (928034-64-4)

Guidance literature:

With 1H-imidazole; dmap; In dichloromethane; at 27 ℃; for 9h;

DOI:10.1002/hlca.200690259

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → N6-benzoyl-5'-O-[(tert-butyl)dimethylsilyl]-8-{[(tert-butyl)diphenylsilyloxy]methyl}-2',3'-O-isopropylideneadenosine (928034-64-4)

Guidance literature:

Multi-step reaction with 3 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

With 1H-imidazole; dmap; n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1002/hlca.200690259

Reference yield:

N-6-benzoyl-2',3'-O-isopropylideneadenosine (39947-04-1) → N6-benzoyl-5'-O-[(tert-butyl)dimethylsilyl]-8-{[(tert-butyl)diphenylsilyloxy]methyl}-2',3'-O-isopropylideneadenosine (928034-64-4)

Guidance literature:

Multi-step reaction with 3 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

With 1H-imidazole; dmap; n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1002/hlca.200690259

upstream raw materials:

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

tert-butylchlorodiphenylsilane

tert-butyldimethylsilyl chloride

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

Downstream raw materials:

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

2',3'-O-isopropylidene-5'-O-(triisopropylsilyl)uridin-6-yl-(6->7'-C)-8-{[(tert-butyl)diphenylsilyloxy]methyl}-9-(6,7-dideoxy-2,3-O-isopropylidene-α-L-talo-hept-6-ynofuranosyl)adenine

2',3'-O-isopropylidene-5'-O-(triisopropylsilyl)uridin-6-yl-(6->7'-C)-8-{[(tert-butyl)diphenylsilyloxy]methyl}-9-(6,7-dideoxy-2,3-O-isopropylidene-β-D-allo-hept-6-ynofuranosyl)adenine

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

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