(4R,6S)-4-Hydroxy-6-(2-methyl-4-phenyl-quinolin-3-yloxymethyl)-tetrahydro-pyran-2-one

Base Information

Chemical Name:(4R,6S)-4-Hydroxy-6-(2-methyl-4-phenyl-quinolin-3-yloxymethyl)-tetrahydro-pyran-2-one
CAS No.:136006-81-0
Molecular Formula:C₂₂H₂₁NO₄
Molecular Weight:363.413
Hs Code.:

Synonyms:(4R,6S)-4-Hydroxy-6-(2-methyl-4-phenyl-quinolin-3-yloxymethyl)-tetrahydro-pyran-2-one

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Chemical Property of (4R,6S)-4-Hydroxy-6-(2-methyl-4-phenyl-quinolin-3-yloxymethyl)-tetrahydro-pyran-2-one

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Technology Process of (4R,6S)-4-Hydroxy-6-(2-methyl-4-phenyl-quinolin-3-yloxymethyl)-tetrahydro-pyran-2-one

There total 8 articles about (4R,6S)-4-Hydroxy-6-(2-methyl-4-phenyl-quinolin-3-yloxymethyl)-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: 83.0%

: 136007-70-0
(4R,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-(2-methyl-4-phenyl-quinolin-3-yloxymethyl)-tetrahydro-pyran-2-one

: 136006-81-0
(4R,6S)-4-Hydroxy-6-(2-methyl-4-phenyl-quinolin-3-yloxymethyl)-tetrahydro-pyran-2-one

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃; for 4h;
DOI:10.1021/jm00114a004

Reference yield:

: 17283-06-6
3-hydroxy-2-methyl-4-phenylquinoline

: 136006-81-0
(4R,6S)-4-Hydroxy-6-(2-methyl-4-phenyl-quinolin-3-yloxymethyl)-tetrahydro-pyran-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: K₂CO₃, hydroquinone / dimethylsulfoxide / 8 h / 55 °C

2: 59 percent / CF₃COOH / tetrahydrofuran; H₂O / 4 h / 60 °C

3: tetra-n-butylammonium iodide, N-iodosuccinimide / CH₂Cl₂ / 20 h / Ambient temperature

4: 83 percent / glacial acetic acid, tetra-n-butylammonium fluoride trihydrate / tetrahydrofuran / 4 h / 20 °C

With N-iodo-succinimide; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; potassium carbonate; acetic acid; hydroquinone; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide;
DOI:10.1021/jm00114a004

Reference yield:

: 110772-23-1
[(2S,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-methanol

: 136006-81-0
(4R,6S)-4-Hydroxy-6-(2-methyl-4-phenyl-quinolin-3-yloxymethyl)-tetrahydro-pyran-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: 98 percent / pyridine / CH₂Cl₂ / 3 h / Ambient temperature

2: 90 percent / NaI / acetone / 24 h / Heating

3: K₂CO₃, hydroquinone / dimethylsulfoxide / 8 h / 55 °C

4: 59 percent / CF₃COOH / tetrahydrofuran; H₂O / 4 h / 60 °C

5: tetra-n-butylammonium iodide, N-iodosuccinimide / CH₂Cl₂ / 20 h / Ambient temperature

6: 83 percent / glacial acetic acid, tetra-n-butylammonium fluoride trihydrate / tetrahydrofuran / 4 h / 20 °C

With pyridine; N-iodo-succinimide; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; potassium carbonate; acetic acid; hydroquinone; trifluoroacetic acid; sodium iodide; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; acetone;
DOI:10.1021/jm00114a004