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

Base Information

• Chemical Name: 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
• CAS No.: 928034-67-7
• Molecular Formula: C₄₂H₄₉N₅O₆Si₂
• Molecular Weight: 776.052

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 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

There total 6 articles about 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 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:

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 (928034-83-7) + 2-triethylsilylacetylene (1777-03-3) → 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 (928034-66-6) + 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 (928034-67-7)

Guidance literature:

With ethylmagnesium bromide; In tetrahydrofuran; at 0 ℃; for 3h;

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}-9-[6,7-dideoxy-2,3-O-isopropylidene-7-C-(trimethylsilyl)-α-L-talo-hept-6-ynofuranosyl]adenine (928034-67-7)

Guidance literature:

Multi-step reaction with 4 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

3: 1.45 g / DCC; CHCl₂CO₂H; DMSO / 3 h / 26 °C

4: 386 mg / EtMgBr / tetrahydrofuran / 3 h / 0 °C

With 1H-imidazole; dichloro-acetic acid; dmap; fluorosilicic acid; ethylmagnesium bromide; dimethyl sulfoxide; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; water; acetonitrile; tert-butyl alcohol; 3: Pfitzner-Moffatt oxidation;

DOI:10.1002/hlca.200690259

Reference yield:

N6-benzoyl-8-{[(tert-butyl)diphenylsilyloxy]methyl}-2',3'-O-isopropylideneadenosine (928034-65-5) → 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 (928034-67-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.45 g / DCC; CHCl₂CO₂H; DMSO / 3 h / 26 °C

2: 386 mg / EtMgBr / tetrahydrofuran / 3 h / 0 °C

With dichloro-acetic acid; ethylmagnesium bromide; dimethyl sulfoxide; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1: Pfitzner-Moffatt oxidation;

DOI:10.1002/hlca.200690259

upstream 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

2-triethylsilylacetylene

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

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

Downstream raw materials:

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-α-L-talo-hept-6-ynofuranosyl)adenine

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