(4R,5S,6S)-6-benzyl-4-hydroxy-5,6-O-isopropylidenedioxy-2-cyclohexen-1-one

Base Information

Chemical Name:(4R,5S,6S)-6-benzyl-4-hydroxy-5,6-O-isopropylidenedioxy-2-cyclohexen-1-one
CAS No.:313548-06-0
Molecular Formula:C₁₆H₁₈O₄
Molecular Weight:274.317
Hs Code.:

Synonyms:(4R,5S,6S)-6-benzyl-4-hydroxy-5,6-O-isopropylidenedioxy-2-cyclohexen-1-one

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Chemical Property of (4R,5S,6S)-6-benzyl-4-hydroxy-5,6-O-isopropylidenedioxy-2-cyclohexen-1-one

Chemical Property:

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Technology Process of (4R,5S,6S)-6-benzyl-4-hydroxy-5,6-O-isopropylidenedioxy-2-cyclohexen-1-one

There total 21 articles about (4R,5S,6S)-6-benzyl-4-hydroxy-5,6-O-isopropylidenedioxy-2-cyclohexen-1-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: 93.0%

: 313548-05-9
(1R,4S,4aR,5R,6S,7S,8aS)-7-benzyl-5-hydroxy-6,7-O-isopropylidenedioxy-1,4,4a,5,6,7,8,8a-octahydro-endo-1,4-methanonaphthalen-8-one

: 313548-06-0
(4R,5S,6S)-6-benzyl-4-hydroxy-5,6-O-isopropylidenedioxy-2-cyclohexen-1-one

Guidance literature:: In diphenylether; reflux;
DOI:10.1016/S0040-4039(00)01312-5

Reference yield:

: C₂₁H₂₂O₅

: 313548-06-0
(4R,5S,6S)-6-benzyl-4-hydroxy-5,6-O-isopropylidenedioxy-2-cyclohexen-1-one

Guidance literature:: Multi-step reaction with 5 steps

1: 92 percent / DMAP / acetonitrile / 25 °C

2: 79 percent / n-Bu₃SnH / AIBN / toluene / 110 °C

3: 89 percent / TMSI / CCl₄ / -10 °C

4: 91 percent / Zn; AcOH / methanol / 60 °C

5: 93 percent / diphenyl ether / reflux

With dmap; trimethylsilyl iodide; tri-n-butyl-tin hydride; acetic acid; zinc; 2,2'-azobis(isobutyronitrile); In methanol; tetrachloromethane; diphenylether; toluene; acetonitrile; 1: Acylation / 2: Reduction / 3: Iodination / 4: Reduction / 5: retro-Diels-Alder;
DOI:10.1016/S0040-4039(00)01312-5

Reference yield:

: C₂₈H₂₆O₆S

: 313548-06-0
(4R,5S,6S)-6-benzyl-4-hydroxy-5,6-O-isopropylidenedioxy-2-cyclohexen-1-one

Guidance literature:: Multi-step reaction with 4 steps

1: 79 percent / n-Bu₃SnH / AIBN / toluene / 110 °C

2: 89 percent / TMSI / CCl₄ / -10 °C

3: 91 percent / Zn; AcOH / methanol / 60 °C

4: 93 percent / diphenyl ether / reflux

With trimethylsilyl iodide; tri-n-butyl-tin hydride; acetic acid; zinc; 2,2'-azobis(isobutyronitrile); In methanol; tetrachloromethane; diphenylether; toluene; 1: Reduction / 2: Iodination / 3: Reduction / 4: retro-Diels-Alder;
DOI:10.1016/S0040-4039(00)01312-5