(4R,6S)-6-{2-[Bis-(4-fluoro-phenyl)-methyl]-4,6-dimethyl-phenoxymethyl}-4-hydroxy-tetrahydro-pyran-2-one

Base Information

• Chemical Name: (4R,6S)-6-{2-[Bis-(4-fluoro-phenyl)-methyl]-4,6-dimethyl-phenoxymethyl}-4-hydroxy-tetrahydro-pyran-2-one
• CAS No.: 110724-52-2
• Molecular Formula: C₂₇H₂₆F₂O₄
• Molecular Weight: 452.498

Synonyms:(4R,6S)-6-{2-[Bis-(4-fluoro-phenyl)-methyl]-4,6-dimethyl-phenoxymethyl}-4-hydroxy-tetrahydro-pyran-2-one

Chemical Property of (4R,6S)-6-{2-[Bis-(4-fluoro-phenyl)-methyl]-4,6-dimethyl-phenoxymethyl}-4-hydroxy-tetrahydro-pyran-2-one

Chemical Property:

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Technology Process of (4R,6S)-6-{2-[Bis-(4-fluoro-phenyl)-methyl]-4,6-dimethyl-phenoxymethyl}-4-hydroxy-tetrahydro-pyran-2-one

There total 12 articles about (4R,6S)-6-{2-[Bis-(4-fluoro-phenyl)-methyl]-4,6-dimethyl-phenoxymethyl}-4-hydroxy-tetrahydro-pyran-2-one 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: 73.0%

(4R,6S)-6-{2-[Bis-(4-fluoro-phenyl)-methyl]-4,6-dimethyl-phenoxymethyl}-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-one (110724-47-5) → (4R,6S)-6-{2-[Bis-(4-fluoro-phenyl)-methyl]-4,6-dimethyl-phenoxymethyl}-4-hydroxy-tetrahydro-pyran-2-one (110724-52-2)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃; for 4h;

DOI:10.1021/jm00114a004

Reference yield:

4-fluorobenzoyl chloride (403-43-0) → (4R,6S)-6-{2-[Bis-(4-fluoro-phenyl)-methyl]-4,6-dimethyl-phenoxymethyl}-4-hydroxy-tetrahydro-pyran-2-one (110724-52-2)

Guidance literature:

Multi-step reaction with 8 steps

1: NaOH / H₂O / 0.5 h

2: AlCl₃ / 2 h / 150 °C

3: tetrahydrofuran

4: H₂, conc. HCl / 10percent Pd/C / acetic acid / 1.5 h / 25 °C / 750.06 Torr

5: K₂CO₃, hydroquinone / dimethylsulfoxide / 3 h / 70 °C

6: glacial acetic acid / tetrahydrofuran / 72 h / Heating

7: CrO₃, pyridine, Celite / CH₂Cl₂ / 1 h / 20 - 25 °C

8: 73 percent / glacial acetic acid, tetra-n-butylammonium fluoride trihydrate / tetrahydrofuran / 4 h / 20 °C

With pyridine; chromium(VI) oxide; hydrogenchloride; sodium hydroxide; aluminium trichloride; Celite; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; acetic acid; hydroquinone; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; acetic acid; dimethyl sulfoxide;

DOI:10.1021/jm00114a004

Reference yield:

4-Fluoro-benzoic acid 2,4-dimethyl-phenyl ester (650621-58-2) → (4R,6S)-6-{2-[Bis-(4-fluoro-phenyl)-methyl]-4,6-dimethyl-phenoxymethyl}-4-hydroxy-tetrahydro-pyran-2-one (110724-52-2)

Guidance literature:

Multi-step reaction with 7 steps

1: AlCl₃ / 2 h / 150 °C

2: tetrahydrofuran

3: H₂, conc. HCl / 10percent Pd/C / acetic acid / 1.5 h / 25 °C / 750.06 Torr

4: K₂CO₃, hydroquinone / dimethylsulfoxide / 3 h / 70 °C

5: glacial acetic acid / tetrahydrofuran / 72 h / Heating

6: CrO₃, pyridine, Celite / CH₂Cl₂ / 1 h / 20 - 25 °C

7: 73 percent / glacial acetic acid, tetra-n-butylammonium fluoride trihydrate / tetrahydrofuran / 4 h / 20 °C

With pyridine; chromium(VI) oxide; hydrogenchloride; aluminium trichloride; Celite; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; acetic acid; hydroquinone; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; acetic acid; dimethyl sulfoxide;

DOI:10.1021/jm00114a004

upstream raw materials:

(4R,6S)-6-{2-[Bis-(4-fluoro-phenyl)-methyl]-4,6-dimethyl-phenoxymethyl}-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-one

4-fluorobenzoyl chloride

[(2S,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-methanol

4-Fluoro-benzoic acid 2,4-dimethyl-phenyl ester

Downstream raw materials:

Sodium; (3R,5S)-6-{2-[bis-(4-fluoro-phenyl)-methyl]-4,6-dimethyl-phenoxy}-3,5-dihydroxy-hexanoate

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