(1S,2R,3R,4S)-2,3-epoxy-6-methyl-1-[(p-tolylsulfonyl)methyl]cyclohex-5-ene-1,4-diol

Base Information

Chemical Name:(1S,2R,3R,4S)-2,3-epoxy-6-methyl-1-[(p-tolylsulfonyl)methyl]cyclohex-5-ene-1,4-diol
CAS No.:851129-88-9
Molecular Formula:C₁₅H₁₈O₅S
Molecular Weight:310.371
Hs Code.:

Synonyms:(1S,2R,3R,4S)-2,3-epoxy-6-methyl-1-[(p-tolylsulfonyl)methyl]cyclohex-5-ene-1,4-diol

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Chemical Property of (1S,2R,3R,4S)-2,3-epoxy-6-methyl-1-[(p-tolylsulfonyl)methyl]cyclohex-5-ene-1,4-diol

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Technology Process of (1S,2R,3R,4S)-2,3-epoxy-6-methyl-1-[(p-tolylsulfonyl)methyl]cyclohex-5-ene-1,4-diol

There total 7 articles about (1S,2R,3R,4S)-2,3-epoxy-6-methyl-1-[(p-tolylsulfonyl)methyl]cyclohex-5-ene-1,4-diol 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: 67.0%

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

: (1S,2R,3R,4R)-2,3-epoxy-6-methyl-1-[(p-tolylsulfonyl)methyl]cyclohex-5-ene-1,4-diol

: 851129-88-9
(1S,2R,3R,4S)-2,3-epoxy-6-methyl-1-[(p-tolylsulfonyl)methyl]cyclohex-5-ene-1,4-diol

Guidance literature:: With diisobutylaluminium hydride; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;
DOI:10.1021/ol050287a DOI:10.1002/chem.200601330

Reference yield:

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

: 851129-88-9
(1S,2R,3R,4S)-2,3-epoxy-6-methyl-1-[(p-tolylsulfonyl)methyl]cyclohex-5-ene-1,4-diol

Guidance literature:: Multi-step reaction with 4 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

4: 67 percent / DIBALH / tetrahydrofuran; hexane / 0.5 h / -78 °C

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

Reference yield:

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

: 851129-88-9
(1S,2R,3R,4S)-2,3-epoxy-6-methyl-1-[(p-tolylsulfonyl)methyl]cyclohex-5-ene-1,4-diol

Guidance literature:: Multi-step reaction with 2 steps

1: 72 percent / benzyltrimethylammonium hydroxide; tert-butyl hydroperoxide / methanol; tetrahydrofuran / 0 °C

2: 67 percent / DIBALH / tetrahydrofuran; hexane / 0.5 h / -78 °C

With tert.-butylhydroperoxide; N-benzyl-trimethylammonium hydroxide; diisobutylaluminium hydride; In tetrahydrofuran; methanol; hexane;
DOI:10.1002/chem.200601330