[(1S,2S,4R,5S)-8,8-Dimethyl-4-(toluene-4-sulfonyl)-6-oxa-bicyclo[3.2.1]oct-2-yl]-methanol

Base Information

Chemical Name:[(1S,2S,4R,5S)-8,8-Dimethyl-4-(toluene-4-sulfonyl)-6-oxa-bicyclo[3.2.1]oct-2-yl]-methanol
CAS No.:184713-05-1
Molecular Formula:C₁₇H₂₄O₄S
Molecular Weight:324.441
Hs Code.:

Synonyms:[(1S,2S,4R,5S)-8,8-Dimethyl-4-(toluene-4-sulfonyl)-6-oxa-bicyclo[3.2.1]oct-2-yl]-methanol

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Chemical Property of [(1S,2S,4R,5S)-8,8-Dimethyl-4-(toluene-4-sulfonyl)-6-oxa-bicyclo[3.2.1]oct-2-yl]-methanol

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Technology Process of [(1S,2S,4R,5S)-8,8-Dimethyl-4-(toluene-4-sulfonyl)-6-oxa-bicyclo[3.2.1]oct-2-yl]-methanol

There total 4 articles about [(1S,2S,4R,5S)-8,8-Dimethyl-4-(toluene-4-sulfonyl)-6-oxa-bicyclo[3.2.1]oct-2-yl]-methanol 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: 86.0%

: 184713-04-0
[(1S,6S)-6-Hydroxymethyl-5,5-dimethyl-3-(toluene-4-sulfonyl)-cyclohex-3-enyl]-methanol

: 184713-05-1
[(1S,2S,4R,5S)-8,8-Dimethyl-4-(toluene-4-sulfonyl)-6-oxa-bicyclo[3.2.1]oct-2-yl]-methanol

Guidance literature:: With ethanol; sodium; for 44h; Ambient temperature;
DOI:10.1021/jo961347g

Reference yield:

: 152836-40-3
(+)-(R)-4-methyl-2-(p-tolylsulfinyl)-1,3-pentadiene

: 184713-05-1
[(1S,2S,4R,5S)-8,8-Dimethyl-4-(toluene-4-sulfonyl)-6-oxa-bicyclo[3.2.1]oct-2-yl]-methanol

Guidance literature:: Multi-step reaction with 4 steps

1: 2.) aq. Na₂CO₃ / 1) THF, reflux, 3 d; 2) THF, rt, 2 h

2: 1.) Et₃N, ClCO₂Et, 2.) NaBH₄, 3.) CaCl₂, NaBH₄ / 1) DME, -7 deg C, 30 min; 2) H₂O, DME, 30 min, rt; 3) EtOH, 45 deg C, 30 min

3: 96 percent / m-CPBA / CH₂Cl₂ / 12 h / Ambient temperature

4: 86 percent / Na, EtOH / 44 h / Ambient temperature

With sodium tetrahydroborate; ethanol; sodium; chloroformic acid ethyl ester; sodium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; calcium chloride; In dichloromethane;
DOI:10.1021/jo961347g

Reference yield:

: 3,3-Dimethyl-5-((S)-toluene-4-sulfinyl)-cyclohex-4-ene-1,2-dicarboxylic acid

: 184713-05-1
[(1S,2S,4R,5S)-8,8-Dimethyl-4-(toluene-4-sulfonyl)-6-oxa-bicyclo[3.2.1]oct-2-yl]-methanol

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) Et₃N, ClCO₂Et, 2.) NaBH₄, 3.) CaCl₂, NaBH₄ / 1) DME, -7 deg C, 30 min; 2) H₂O, DME, 30 min, rt; 3) EtOH, 45 deg C, 30 min

2: 96 percent / m-CPBA / CH₂Cl₂ / 12 h / Ambient temperature

3: 86 percent / Na, EtOH / 44 h / Ambient temperature

With sodium tetrahydroborate; ethanol; sodium; chloroformic acid ethyl ester; triethylamine; 3-chloro-benzenecarboperoxoic acid; calcium chloride; In dichloromethane;
DOI:10.1021/jo961347g