9-[1',3'-O-anhydro-6'-O-(4,4'-dimethoxytrityl)-β-D-psicofuranosyl]-N⁶-(phenoxyacetyl)adenine

Base Information

• Chemical Name: 9-[1',3'-O-anhydro-6'-O-(4,4'-dimethoxytrityl)-β-D-psicofuranosyl]-N⁶-(phenoxyacetyl)adenine
• CAS No.: 783322-66-7
• Molecular Formula: C₄₀H₃₇N₅O₈
• Molecular Weight: 715.762

Synonyms:9-[1',3'-O-anhydro-6'-O-(4,4'-dimethoxytrityl)-β-D-psicofuranosyl]-N⁶-(phenoxyacetyl)adenine

Chemical Property of 9-[1',3'-O-anhydro-6'-O-(4,4'-dimethoxytrityl)-β-D-psicofuranosyl]-N⁶-(phenoxyacetyl)adenine

Chemical Property:

Purity/Quality:

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Technology Process of 9-[1',3'-O-anhydro-6'-O-(4,4'-dimethoxytrityl)-β-D-psicofuranosyl]-N⁶-(phenoxyacetyl)adenine

There total 18 articles about 9-[1',3'-O-anhydro-6'-O-(4,4'-dimethoxytrityl)-β-D-psicofuranosyl]-N⁶-(phenoxyacetyl)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-benzoyladenine (4005-49-6) → 9-[1',3'-O-anhydro-6'-O-(4,4'-dimethoxytrityl)-β-D-psicofuranosyl]-N6-(phenoxyacetyl)adenine (783322-66-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: Me₃SiCl; hexamethyldisilazane / 12 h / 120 °C

1.2: 6.1 g / SnCl₄ / 1,2-dichloro-ethane; acetonitrile / 3 h / 70 °C

2.1: NH₃ / methanol / 48 h / 20 °C

3.1: 4.1 g / pyridine / 2.5 h / 0 - 20 °C

4.1: 81 percent / NaHMDS / tetrahydrofuran / 2 h / 4 °C

5.1: 60 percent / pyridine / 3 h / 20 °C

6.1: TBAF / tetrahydrofuran / 0.07 h / 20 °C

7.1: 1.54 g / pyridine / 20 °C

With pyridine; chloro-trimethyl-silane; tetrabutyl ammonium fluoride; ammonia; sodium hexamethyldisilazane; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; methanol;

DOI:10.1021/ja048417i

Reference yield:

6-O-(4-toluoyl)-1,2:3,4-di-O-isopropylidene-β-D-psicofuranose (344905-99-3) → 9-[1',3'-O-anhydro-6'-O-(4,4'-dimethoxytrityl)-β-D-psicofuranosyl]-N6-(phenoxyacetyl)adenine (783322-66-7)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 60 percent / HCl

2.1: pyridine / 12 h / 4 °C

3.1: aq. TFA / 0.42 h / 20 °C

4.1: 5.3 g / pyridine / 3 h / 20 °C

5.1: HBr; AcOH / CH₂Cl₂ / 12 h / 0 - 20 °C

6.1: Me₃SiCl; hexamethyldisilazane / 12 h / 120 °C

6.2: 6.1 g / SnCl₄ / 1,2-dichloro-ethane; acetonitrile / 3 h / 70 °C

7.1: NH₃ / methanol / 48 h / 20 °C

8.1: 4.1 g / pyridine / 2.5 h / 0 - 20 °C

9.1: 81 percent / NaHMDS / tetrahydrofuran / 2 h / 4 °C

10.1: 60 percent / pyridine / 3 h / 20 °C

11.1: TBAF / tetrahydrofuran / 0.07 h / 20 °C

12.1: 1.54 g / pyridine / 20 °C

With pyridine; hydrogenchloride; chloro-trimethyl-silane; tetrabutyl ammonium fluoride; ammonia; hydrogen bromide; sodium hexamethyldisilazane; acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ja048417i

Reference yield:

9-[1'-O-methanesulfonyl-3',4'-O-acetyl-6'-O-(4-toluoyl)-β-D-psicofuranosyl]-N6-benzoyladenine (478487-96-6) → 9-[1',3'-O-anhydro-6'-O-(4,4'-dimethoxytrityl)-β-D-psicofuranosyl]-N6-(phenoxyacetyl)adenine (783322-66-7)

Guidance literature:

Multi-step reaction with 6 steps

1: NH₃ / methanol / 48 h / 20 °C

2: 4.1 g / pyridine / 2.5 h / 0 - 20 °C

3: 81 percent / NaHMDS / tetrahydrofuran / 2 h / 4 °C

4: 60 percent / pyridine / 3 h / 20 °C

5: TBAF / tetrahydrofuran / 0.07 h / 20 °C

6: 1.54 g / pyridine / 20 °C

With pyridine; tetrabutyl ammonium fluoride; ammonia; sodium hexamethyldisilazane; In tetrahydrofuran; methanol;

DOI:10.1021/ja048417i

upstream raw materials:

4,4'-dimethoxytrityl chloride

9-[6'-O-benzyl-1',3'-O-anhydro-β-D-psicofuranosyl]adenine

9-[6'-O-benzyl-1'-O-(4-toluenosulfonyl)-β-D-psicofuranosyl]adenine

9-(1',3'-O-anhydro-β-D-psicofuranosyl)adenine

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