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

Base Information

Chemical Name:8-{[(tert-butyl)diphenylsilyloxy]methyl}-9-[6,7-dideoxy-2,3-O-isopropylidene-β-D-allo-hept-6-ynofuranosyl]adenine
CAS No.:928034-68-8
Molecular Formula:C₃₂H₃₇N₅O₅Si
Molecular Weight:599.762
Hs Code.:

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

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

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

There total 8 articles about 8-{[(tert-butyl)diphenylsilyloxy]methyl}-9-[6,7-dideoxy-2,3-O-isopropylidene-β-D-allo-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-(1-hydroxy-prop-2-ynyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-9H-purin-6-yl}-benzamide

: 928034-68-8
8-{[(tert-butyl)diphenylsilyloxy]methyl}-9-[6,7-dideoxy-2,3-O-isopropylidene-β-D-allo-hept-6-ynofuranosyl]adenine

Guidance literature:: With methylamine; In tetrahydrofuran; ethanol; for 6h;
DOI:10.1002/hlca.200690259

Reference yield:

: 928034-63-3
N⁶-benzoyl-5'-O-[(tert-butyl)dimethylsilyl]-8-(hydroxymethyl)-2',3'-O-isopropylideneadenosine

: 928034-68-8
8-{[(tert-butyl)diphenylsilyloxy]methyl}-9-[6,7-dideoxy-2,3-O-isopropylidene-β-D-allo-hept-6-ynofuranosyl]adenine

Guidance literature:: Multi-step reaction with 6 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: 772 mg / EtMgBr / tetrahydrofuran / 3 h / 0 °C

5: K₂CO₃ / methanol / 6 h / 0 °C

6: 491 mg / MeNH₂ / ethanol; tetrahydrofuran / 6 h

With 1H-imidazole; dichloro-acetic acid; dmap; fluorosilicic acid; ethylmagnesium bromide; potassium carbonate; dimethyl sulfoxide; dicyclohexyl-carbodiimide; methylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetonitrile; tert-butyl alcohol; 3: Pfitzner-Moffatt oxidation;
DOI:10.1002/hlca.200690259

Reference yield:

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

: 928034-68-8
8-{[(tert-butyl)diphenylsilyloxy]methyl}-9-[6,7-dideoxy-2,3-O-isopropylidene-β-D-allo-hept-6-ynofuranosyl]adenine

Guidance literature:: Multi-step reaction with 4 steps

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

2: 772 mg / EtMgBr / tetrahydrofuran / 3 h / 0 °C

3: K₂CO₃ / methanol / 6 h / 0 °C

4: 491 mg / MeNH₂ / ethanol; tetrahydrofuran / 6 h

With dichloro-acetic acid; ethylmagnesium bromide; potassium carbonate; dimethyl sulfoxide; dicyclohexyl-carbodiimide; methylamine; In tetrahydrofuran; methanol; ethanol; 1: Pfitzner-Moffatt oxidation;
DOI:10.1002/hlca.200690259