6-N-benzoyl-9-(2,5-di-O-(tert-butyldimethylsilyl)-3-C-vinyl-β-D-xylofuranosyl)adenine

Base Information

Chemical Name:6-N-benzoyl-9-(2,5-di-O-(tert-butyldimethylsilyl)-3-C-vinyl-β-D-xylofuranosyl)adenine
CAS No.:188486-28-4
Molecular Formula:C₃₁H₄₇N₅O₅Si₂
Molecular Weight:625.916
Hs Code.:

Synonyms:6-N-benzoyl-9-(2,5-di-O-(tert-butyldimethylsilyl)-3-C-vinyl-β-D-xylofuranosyl)adenine

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Chemical Property of 6-N-benzoyl-9-(2,5-di-O-(tert-butyldimethylsilyl)-3-C-vinyl-β-D-xylofuranosyl)adenine

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Technology Process of 6-N-benzoyl-9-(2,5-di-O-(tert-butyldimethylsilyl)-3-C-vinyl-β-D-xylofuranosyl)adenine

There total 6 articles about 6-N-benzoyl-9-(2,5-di-O-(tert-butyldimethylsilyl)-3-C-vinyl-β-D-xylofuranosyl)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:

: 9-(3-C-phenylselenocarbonyl-β-D-xylofuranosyl)adenine

: 188486-28-4
6-N-benzoyl-9-(2,5-di-O-(tert-butyldimethylsilyl)-3-C-vinyl-β-D-xylofuranosyl)adenine

Guidance literature:: Multi-step reaction with 7 steps

1.1: Bu₃SnH / methanol / 2.5 h / 20 °C / Photolysis

2.1: 50 percent / pyridine / 20 °C

3.1: 100 percent / pyridine / 1 h / 0 - 20 °C

4.1: 100 percent / pyridine / 2 h / 0 - 20 °C

5.1: 100 percent / p-toluenesulfonic acid; EtOH / 1 h / 0 - 20 °C

6.1: 99 percent / Dess-Martin periodinane / CH₂Cl₂ / 72 h / 0 - 20 °C

7.1: CeCl₃ / tetrahydrofuran / 4 h / -78 °C

7.2: 82 percent / tetrahydrofuran / 3 h / -78 °C

With pyridine; cerium(III) chloride; ethanol; tri-n-butyl-tin hydride; Dess-Martin periodane; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; 1.1: Reduction / 2.1: silylation / 3.1: silylation / 4.1: benzoylation / 5.1: desilylation / 6.1: Oxidation / 7.1: transmetallation / 7.2: Addition;
DOI:10.1021/ja962974q

Reference yield:

: 65109-11-7
2',5'-bis-O-(tert-butyldimethylsilyl)adenosine

: 188486-28-4
6-N-benzoyl-9-(2,5-di-O-(tert-butyldimethylsilyl)-3-C-vinyl-β-D-xylofuranosyl)adenine

Guidance literature:: Multi-step reaction with 5 steps

1.1: 100 percent / pyridine / 1 h / 0 - 20 °C

2.1: 100 percent / pyridine / 2 h / 0 - 20 °C

3.1: 100 percent / p-toluenesulfonic acid; EtOH / 1 h / 0 - 20 °C

4.1: 99 percent / Dess-Martin periodinane / CH₂Cl₂ / 72 h / 0 - 20 °C

5.1: CeCl₃ / tetrahydrofuran / 4 h / -78 °C

5.2: 82 percent / tetrahydrofuran / 3 h / -78 °C

With pyridine; cerium(III) chloride; ethanol; Dess-Martin periodane; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; 1.1: silylation / 2.1: benzoylation / 3.1: desilylation / 4.1: Oxidation / 5.1: transmetallation / 5.2: Addition;
DOI:10.1021/ja962974q

Reference yield:

: 9-[3-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-trimethylsilanyloxy-tetrahydro-furan-2-yl]-9H-purin-6-ylamine

: 188486-28-4
6-N-benzoyl-9-(2,5-di-O-(tert-butyldimethylsilyl)-3-C-vinyl-β-D-xylofuranosyl)adenine

Guidance literature:: Multi-step reaction with 4 steps

1.1: 100 percent / pyridine / 2 h / 0 - 20 °C

2.1: 100 percent / p-toluenesulfonic acid; EtOH / 1 h / 0 - 20 °C

3.1: 99 percent / Dess-Martin periodinane / CH₂Cl₂ / 72 h / 0 - 20 °C

4.1: CeCl₃ / tetrahydrofuran / 4 h / -78 °C

4.2: 82 percent / tetrahydrofuran / 3 h / -78 °C

With pyridine; cerium(III) chloride; ethanol; Dess-Martin periodane; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; 1.1: benzoylation / 2.1: desilylation / 3.1: Oxidation / 4.1: transmetallation / 4.2: Addition;
DOI:10.1021/ja962974q