(4S,6S)-6-[2-(4-Benzyloxy-phenyl)-ethyl]-4-hydroxy-tetrahydro-pyran-2-one

Base Information

Chemical Name:(4S,6S)-6-[2-(4-Benzyloxy-phenyl)-ethyl]-4-hydroxy-tetrahydro-pyran-2-one
CAS No.:885118-04-7
Molecular Formula:C₂₀H₂₂O₄
Molecular Weight:326.392
Hs Code.:

Synonyms:(4S,6S)-6-[2-(4-Benzyloxy-phenyl)-ethyl]-4-hydroxy-tetrahydro-pyran-2-one

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Chemical Property of (4S,6S)-6-[2-(4-Benzyloxy-phenyl)-ethyl]-4-hydroxy-tetrahydro-pyran-2-one

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Technology Process of (4S,6S)-6-[2-(4-Benzyloxy-phenyl)-ethyl]-4-hydroxy-tetrahydro-pyran-2-one

There total 1 articles about (4S,6S)-6-[2-(4-Benzyloxy-phenyl)-ethyl]-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:

: 885118-01-4
(S)-6-[(4-benzyloxy)phenethyl]-5,6-dihydropyran-2-one

: 885118-04-7
(4S,6S)-6-[2-(4-Benzyloxy-phenyl)-ethyl]-4-hydroxy-tetrahydro-pyran-2-one

Guidance literature:: (S)-6-[(4-benzyloxy)phenethyl]-5,6-dihydropyran-2-one; With sodium hydroxide; dihydrogen peroxide; In ethanol; at 0 ℃; for 2h;

With pyridinium p-toluenesulfonate; In toluene; for 2h; Heating;

With sodium tetrahydroborate; diphenyl diselenide; In ethanol; at 0 ℃; for 2h;
DOI:10.1016/j.tetlet.2006.01.159

Reference yield: 62.0%

: 885118-04-7
(4S,6S)-6-[2-(4-Benzyloxy-phenyl)-ethyl]-4-hydroxy-tetrahydro-pyran-2-one

: 885118-05-8
(S)-6-[2-(4-Benzyloxy-phenyl)-ethyl]-dihydro-pyran-2,4-dione

Guidance literature:: With pyridinium chlorochromate; In dichloromethane; at 0 - 20 ℃; for 12h;
DOI:10.1016/j.tetlet.2006.01.159

Reference yield:

: 885118-04-7
(4S,6S)-6-[2-(4-Benzyloxy-phenyl)-ethyl]-4-hydroxy-tetrahydro-pyran-2-one

: (4R,6S)-6-[2-(4-Benzyloxy-phenyl)-ethyl]-4-(3-bromo-4-methoxy-2,6-bis-methoxymethoxy-phenyl)-tetrahydro-pyran-2-one

Guidance literature:: Multi-step reaction with 7 steps

1: 62 percent / PCC / CH₂Cl₂ / 12 h / 0 - 20 °C

2: 74 percent / NEt₃ / CH₂Cl₂ / 0.5 h / -78 °C

3: 98 percent / aq. K₂CO₃ / PdCl₂(PPh₃)2 / tetrahydrofuran / 3 h / Heating

4: 92 percent / hydrogen / Pd/C / ethyl acetate; ethanol / 45 h / 20 °C

5: 76 percent / hydrogen / Pd/C / ethyl acetate; ethanol / 72 h / 20 °C

6: 87 percent / NaH / dimethylformamide / 1 h / 0 °C

7: 94 percent / NBS / CH₂Cl₂ / 3 h / 20 °C

With N-Bromosuccinimide; hydrogen; sodium hydride; potassium carbonate; triethylamine; pyridinium chlorochromate; bis-triphenylphosphine-palladium(II) chloride; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 3: Suzuki coupling;
DOI:10.1016/j.tetlet.2006.01.159