6-N-benzoyl-9-(2-O-acetyl-3,5-O-isopropylidene-3-C-phenylselenocarbonyl-β-D-xylofuranosyl)adenine

Base Information

Chemical Name:6-N-benzoyl-9-(2-O-acetyl-3,5-O-isopropylidene-3-C-phenylselenocarbonyl-β-D-xylofuranosyl)adenine
CAS No.:188486-40-0
Molecular Formula:C₂₉H₂₇N₅O₇Se
Molecular Weight:636.523
Hs Code.:

Synonyms:6-N-benzoyl-9-(2-O-acetyl-3,5-O-isopropylidene-3-C-phenylselenocarbonyl-β-D-xylofuranosyl)adenine

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Chemical Property of 6-N-benzoyl-9-(2-O-acetyl-3,5-O-isopropylidene-3-C-phenylselenocarbonyl-β-D-xylofuranosyl)adenine

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Technology Process of 6-N-benzoyl-9-(2-O-acetyl-3,5-O-isopropylidene-3-C-phenylselenocarbonyl-β-D-xylofuranosyl)adenine

There total 13 articles about 6-N-benzoyl-9-(2-O-acetyl-3,5-O-isopropylidene-3-C-phenylselenocarbonyl-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: 72.0%

: 645-96-5
Benzeneselenol

: 188486-39-7
6-N-benzoyl-9-(2-O-acetyl-3-C-carboxy-3,5-O-isopropylidene-β-D-xylofuranosyl)adenine

: 188486-40-0
6-N-benzoyl-9-(2-O-acetyl-3,5-O-isopropylidene-3-C-phenylselenocarbonyl-β-D-xylofuranosyl)adenine

Guidance literature:: 6-N-benzoyl-9-(2-O-acetyl-3-C-carboxy-3,5-O-isopropylidene-β-D-xylofuranosyl)adenine; With O-phenyl phosphorodichloridate; triethylamine; In tetrahydrofuran; at 0 ℃; for 1h;

Benzeneselenol; With triethylamine; In tetrahydrofuran; at 0 ℃; for 0.5h;
DOI:10.1021/ja962974q

Reference yield:

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

: 188486-40-0
6-N-benzoyl-9-(2-O-acetyl-3,5-O-isopropylidene-3-C-phenylselenocarbonyl-β-D-xylofuranosyl)adenine

Guidance literature:: Multi-step reaction with 13 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

8.1: 82 percent / TBAF / tetrahydrofuran / 3 h / 0 °C

9.1: 99 percent / AlCl₃ / diethyl ether / 1 h / 0 - 20 °C

10.1: 97 percent / pyridine / 0 - 20 °C

11.1: ozone / CH₂Cl₂ / 1 h / -78 °C

11.2: 69 percent / Me₂S / CH₂Cl₂ / 1 h / -78 - 20 °C

12.1: 91 percent / KMnO₄; phosphate buffer / 2-methyl-propan-2-ol; H₂O / 0.5 h / 20 °C / pH 7

13.1: NEt₃; phenyl dichlorophosphate / tetrahydrofuran / 1 h / 0 °C

13.2: 72 percent / NEt₃ / tetrahydrofuran / 0.5 h / 0 °C

With pyridine; potassium permanganate; aluminium trichloride; phosphate buffer; cerium(III) chloride; ethanol; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; Dess-Martin periodane; toluene-4-sulfonic acid; ozone; O-phenyl phosphorodichloridate; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; tert-butyl alcohol; 1.1: Reduction / 2.1: silylation / 3.1: silylation / 4.1: benzoylation / 5.1: desilylation / 6.1: Oxidation / 7.1: transmetallation / 7.2: Addition / 8.1: desilylation / 9.1: acetonidation / 10.1: Acetylation / 11.1: ozonolysis / 11.2: Reduction / 12.1: Oxidation / 13.1: phosphorylation / 13.2: Acylation;
DOI:10.1021/ja962974q

Reference yield:

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

: 188486-40-0
6-N-benzoyl-9-(2-O-acetyl-3,5-O-isopropylidene-3-C-phenylselenocarbonyl-β-D-xylofuranosyl)adenine

Guidance literature:: Multi-step reaction with 11 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

6.1: 82 percent / TBAF / tetrahydrofuran / 3 h / 0 °C

7.1: 99 percent / AlCl₃ / diethyl ether / 1 h / 0 - 20 °C

8.1: 97 percent / pyridine / 0 - 20 °C

9.1: ozone / CH₂Cl₂ / 1 h / -78 °C

9.2: 69 percent / Me₂S / CH₂Cl₂ / 1 h / -78 - 20 °C

10.1: 91 percent / KMnO₄; phosphate buffer / 2-methyl-propan-2-ol; H₂O / 0.5 h / 20 °C / pH 7

11.1: NEt₃; phenyl dichlorophosphate / tetrahydrofuran / 1 h / 0 °C

11.2: 72 percent / NEt₃ / tetrahydrofuran / 0.5 h / 0 °C

With pyridine; potassium permanganate; aluminium trichloride; phosphate buffer; cerium(III) chloride; ethanol; tetrabutyl ammonium fluoride; Dess-Martin periodane; toluene-4-sulfonic acid; ozone; O-phenyl phosphorodichloridate; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; water; tert-butyl alcohol; 1.1: silylation / 2.1: benzoylation / 3.1: desilylation / 4.1: Oxidation / 5.1: transmetallation / 5.2: Addition / 6.1: desilylation / 7.1: acetonidation / 8.1: Acetylation / 9.1: ozonolysis / 9.2: Reduction / 10.1: Oxidation / 11.1: phosphorylation / 11.2: Acylation;
DOI:10.1021/ja962974q