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

Base Information

• Chemical Name: 9-[1',3'-O-anhydro-4',6'-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-psicofuranosyl]-N⁶-(phenoxyacetyl)-adenine
• CAS No.: 783322-65-6
• Molecular Formula: C₃₁H₄₅N₅O₇Si₂
• Molecular Weight: 655.899

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

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

Chemical Property:

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

There total 11 articles about 9-[1',3'-O-anhydro-4',6'-O-(tetraisopropyldisiloxane-1,3-diyl)-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: 60.0%

Phenoxyacetyl chloride (701-99-5) + 9-[1',3'-O-anhydro-4',6'-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-psicofuranosyl]adenine (783322-64-5) → 9-[1',3'-O-anhydro-4',6'-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-psicofuranosyl]-N6-(phenoxyacetyl)-adenine (783322-65-6)

Guidance literature:

With pyridine; at 20 ℃; for 3h;

DOI:10.1021/ja048417i

Reference yield:

N-benzoyladenine (4005-49-6) → 9-[1',3'-O-anhydro-4',6'-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-psicofuranosyl]-N6-(phenoxyacetyl)-adenine (783322-65-6)

Guidance literature:

Multi-step reaction with 5 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

With pyridine; chloro-trimethyl-silane; 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-4',6'-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-psicofuranosyl]-N6-(phenoxyacetyl)-adenine (783322-65-6)

Guidance literature:

Multi-step reaction with 10 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

With pyridine; hydrogenchloride; chloro-trimethyl-silane; 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

upstream raw materials:

Phenoxyacetyl chloride

9-[1',3'-O-anhydro-4',6'-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-psicofuranosyl]adenine

N-benzoyladenine

6-O-(4-toluoyl)-1,2:3,4-di-O-isopropylidene-β-D-psicofuranose

Downstream raw materials:

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

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