(2S,3R,4S)-2,3-epoxy-4-hydroxy-5-methyl-4-[(p-tolylsulfonyl)methyl]-5-cyclohexen-1-one

Base Information

Chemical Name:(2S,3R,4S)-2,3-epoxy-4-hydroxy-5-methyl-4-[(p-tolylsulfonyl)methyl]-5-cyclohexen-1-one
CAS No.:851129-86-7
Molecular Formula:C₁₅H₁₆O₅S
Molecular Weight:308.355
Hs Code.:

Synonyms:(2S,3R,4S)-2,3-epoxy-4-hydroxy-5-methyl-4-[(p-tolylsulfonyl)methyl]-5-cyclohexen-1-one

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Chemical Property of (2S,3R,4S)-2,3-epoxy-4-hydroxy-5-methyl-4-[(p-tolylsulfonyl)methyl]-5-cyclohexen-1-one

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Technology Process of (2S,3R,4S)-2,3-epoxy-4-hydroxy-5-methyl-4-[(p-tolylsulfonyl)methyl]-5-cyclohexen-1-one

There total 6 articles about (2S,3R,4S)-2,3-epoxy-4-hydroxy-5-methyl-4-[(p-tolylsulfonyl)methyl]-5-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: 72.0%

: 851129-84-5
(4R)-4-hydroxy-3-methyl-4-[(p-tolylsulfonyl)methyl]-2,5-cyclohexadien-1-one

: 851129-86-7
(2S,3R,4S)-2,3-epoxy-4-hydroxy-5-methyl-4-[(p-tolylsulfonyl)methyl]-5-cyclohexen-1-one

Guidance literature:: With tert.-butylhydroperoxide; N-benzyl-trimethylammonium hydroxide; In tetrahydrofuran; methanol; decane; at 0 ℃; for 2h;
DOI:10.1021/ol050287a

Reference yield:

: 851129-82-3
(4R,5R)-6-Bromo-4-hydroxy-5-methyl-4-((R)-toluene-4-sulfinylmethyl)-cyclohex-2-enone

: 851129-86-7
(2S,3R,4S)-2,3-epoxy-4-hydroxy-5-methyl-4-[(p-tolylsulfonyl)methyl]-5-cyclohexen-1-one

Guidance literature:: Multi-step reaction with 3 steps

1: Li₂CO₃; LiBr / dimethylformamide / 100 °C

2: 99 percent / meta-chloroperbenzoic acid / CH₂Cl₂ / 0 °C

3: 72 percent / benzyltrimethylammonium hydroxide; tert-butyl hydroperoxide / methanol; tetrahydrofuran / 0 °C

With tert.-butylhydroperoxide; N-benzyl-trimethylammonium hydroxide; lithium carbonate; 3-chloro-benzenecarboperoxoic acid; lithium bromide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/chem.200601330

Reference yield:

: 170117-33-6
[(S)R]-4-hydroxy-4-[p-(tolylsulfinyl)methyl]cyclohexa-2,5-dienone

: 851129-86-7
(2S,3R,4S)-2,3-epoxy-4-hydroxy-5-methyl-4-[(p-tolylsulfonyl)methyl]-5-cyclohexen-1-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: CH₂Cl₂ / -78 °C

1.2: N-bromosuccinimide / tetrahydrofuran / -78 °C

2.1: Li₂CO₃; LiBr / dimethylformamide / 100 °C

3.1: 99 percent / meta-chloroperbenzoic acid / CH₂Cl₂ / 0 °C

4.1: 72 percent / benzyltrimethylammonium hydroxide; tert-butyl hydroperoxide / methanol; tetrahydrofuran / 0 °C

With tert.-butylhydroperoxide; N-benzyl-trimethylammonium hydroxide; lithium carbonate; 3-chloro-benzenecarboperoxoic acid; lithium bromide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/chem.200601330