(6S)-6-[(2R,4S)-2-hydroxy-4-methoxy-4-phenylbutyl]-5,6-dihydro-2H-pyran-2-one

Base Information

Chemical Name:(6S)-6-[(2R,4S)-2-hydroxy-4-methoxy-4-phenylbutyl]-5,6-dihydro-2H-pyran-2-one
CAS No.:1448463-83-9
Molecular Formula:C₁₆H₂₀O₄
Molecular Weight:276.332
Hs Code.:

Synonyms:(6S)-6-[(2R,4S)-2-hydroxy-4-methoxy-4-phenylbutyl]-5,6-dihydro-2H-pyran-2-one

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Chemical Property of (6S)-6-[(2R,4S)-2-hydroxy-4-methoxy-4-phenylbutyl]-5,6-dihydro-2H-pyran-2-one

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Technology Process of (6S)-6-[(2R,4S)-2-hydroxy-4-methoxy-4-phenylbutyl]-5,6-dihydro-2H-pyran-2-one

There total 10 articles about (6S)-6-[(2R,4S)-2-hydroxy-4-methoxy-4-phenylbutyl]-5,6-dihydro-2H-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: 90.0%

: 1448464-06-9
(6S)-6-[(2R,4S)-2-(tert-butyldimethylsilyloxy)-4-methoxy-4-phenylbutyl]-5,6-dihydro-2H-pyran-2-one

: 1448463-83-9
(6S)-6-[(2R,4S)-2-hydroxy-4-methoxy-4-phenylbutyl]-5,6-dihydro-2H-pyran-2-one

Guidance literature:: With pyridinium p-toluenesulfonate; In methanol; water; for 18h; Reflux;
DOI:10.1002/ejoc.201201283

Reference yield:

: 77118-87-7,936-58-3
(S)-1-Phenyl-3-buten-1-ol

: 1448463-83-9
(6S)-6-[(2R,4S)-2-hydroxy-4-methoxy-4-phenylbutyl]-5,6-dihydro-2H-pyran-2-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: sodium hydride / tetrahydrofuran / 20 °C / Inert atmosphere; Cooling with ice

1.2: 20 °C / Inert atmosphere

2.1: oxygen; ozone / dichloromethane / -78 °C

2.2: -78 - 20 °C

3.1: B-chlorodiisopinocampheylborane / diethyl ether / -78 °C / Inert atmosphere

3.2: -78 °C / Inert atmosphere

4.1: 2,6-dimethylpyridine / dichloromethane / 1 h / 20 °C / Inert atmosphere

5.1: oxygen; ozone / dichloromethane / -78 °C

5.2: -78 - 20 °C

6.1: (-)-diisopinocamphenylborane chloride / diethyl ether / -78 °C / Inert atmosphere

6.2: -78 °C / Inert atmosphere

7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / -78 °C / Inert atmosphere

8.1: Grubbs catalyst first generation / dichloromethane / Inert atmosphere; Reflux

9.1: pyridinium p-toluenesulfonate / methanol; water / 18 h / Reflux

With 2,6-dimethylpyridine; Grubbs catalyst first generation; oxygen; pyridinium p-toluenesulfonate; sodium hydride; ozone; N-ethyl-N,N-diisopropylamine; (-)-diisopinocamphenylborane chloride; B-chlorodiisopinocampheylborane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water;
DOI:10.1002/ejoc.201201283

Reference yield:

: 865777-28-2
(S)-3-methoxy-3-phenyl-propionaldehyde

: 1448463-83-9
(6S)-6-[(2R,4S)-2-hydroxy-4-methoxy-4-phenylbutyl]-5,6-dihydro-2H-pyran-2-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: B-chlorodiisopinocampheylborane / diethyl ether / -78 °C / Inert atmosphere

1.2: -78 °C / Inert atmosphere

2.1: 2,6-dimethylpyridine / dichloromethane / 1 h / 20 °C / Inert atmosphere

3.1: oxygen; ozone / dichloromethane / -78 °C

3.2: -78 - 20 °C

4.1: (-)-diisopinocamphenylborane chloride / diethyl ether / -78 °C / Inert atmosphere

4.2: -78 °C / Inert atmosphere

5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / -78 °C / Inert atmosphere

6.1: Grubbs catalyst first generation / dichloromethane / Inert atmosphere; Reflux

7.1: pyridinium p-toluenesulfonate / methanol; water / 18 h / Reflux

With 2,6-dimethylpyridine; Grubbs catalyst first generation; oxygen; pyridinium p-toluenesulfonate; ozone; N-ethyl-N,N-diisopropylamine; (-)-diisopinocamphenylborane chloride; B-chlorodiisopinocampheylborane; In methanol; diethyl ether; dichloromethane; water;
DOI:10.1002/ejoc.201201283