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

Base Information

• Chemical Name: N⁶-benzoyl-5'-O-[(tert-butyl)dimethylsilyl]-8-(hydroxymethyl)-2',3'-O-isopropylideneadenosine
• CAS No.: 928034-63-3
• Molecular Formula: C₂₇H₃₇N₅O₆Si
• Molecular Weight: 555.706

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

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

Chemical Property:

Purity/Quality:

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

There total 3 articles about N⁶-benzoyl-5'-O-[(tert-butyl)dimethylsilyl]-8-(hydroxymethyl)-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: 83.0%

N,N-dimethyl-formamide (68-12-2,33513-42-7) + N6-benzoyl-5'-O-[(tert-butyl)dimethylsilyl]-2',3'-O-isopropylideneadenosine (135947-30-7) → N6-benzoyl-5'-O-[(tert-butyl)dimethylsilyl]-8-(hydroxymethyl)-2',3'-O-isopropylideneadenosine (928034-63-3)

Guidance literature:

N⁶-benzoyl-5'-O-[(tert-butyl)dimethylsilyl]-2',3'-O-isopropylideneadenosine; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -76 ℃; for 3h;

N,N-dimethyl-formamide; In tetrahydrofuran; hexane; at -76 ℃; for 3h;

With sodium tetrahydroborate; In tetrahydrofuran; ethanol; hexane; at 27 ℃; for 3h;

DOI:10.1002/hlca.200690259

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → N6-benzoyl-5'-O-[(tert-butyl)dimethylsilyl]-8-(hydroxymethyl)-2',3'-O-isopropylideneadenosine (928034-63-3)

Guidance literature:

Multi-step reaction with 2 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

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-(hydroxymethyl)-2',3'-O-isopropylideneadenosine (928034-63-3)

Guidance literature:

Multi-step reaction with 2 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

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

DOI:10.1002/hlca.200690259

upstream raw materials:

N,N-dimethyl-formamide

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

tert-butyldimethylsilyl chloride

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

Downstream raw materials:

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

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

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

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