trans,cis-3,5-dimethyl-1-phenylthio-trans,cis,cis-2,3,4-trihydroxycyclohexane 3,4-acetonide

Base Information

Chemical Name:trans,cis-3,5-dimethyl-1-phenylthio-trans,cis,cis-2,3,4-trihydroxycyclohexane 3,4-acetonide
CAS No.:81939-86-8
Molecular Formula:C₁₇H₂₄O₃S
Molecular Weight:308.442
Hs Code.:

Synonyms:trans,cis-3,5-dimethyl-1-phenylthio-trans,cis,cis-2,3,4-trihydroxycyclohexane 3,4-acetonide

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Chemical Property of trans,cis-3,5-dimethyl-1-phenylthio-trans,cis,cis-2,3,4-trihydroxycyclohexane 3,4-acetonide

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Technology Process of trans,cis-3,5-dimethyl-1-phenylthio-trans,cis,cis-2,3,4-trihydroxycyclohexane 3,4-acetonide

There total 5 articles about trans,cis-3,5-dimethyl-1-phenylthio-trans,cis,cis-2,3,4-trihydroxycyclohexane 3,4-acetonide 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: 97.0%

: 81939-85-7
β-1,2-epoxy-α-cis-3,4-dihydroxy-trans-3,5-dimethylcyclohexane 3,4-acetonide

: 108-98-5
thiophenol

: 81939-86-8
trans,cis-3,5-dimethyl-1-phenylthio-trans,cis,cis-2,3,4-trihydroxycyclohexane 3,4-acetonide

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 140 ℃; for 24h;
DOI:10.1021/jo00137a018

Reference yield:

: 81939-80-2
cis-3,4-dihydroxy-trans-3,5-dimethylcyclohexene 3,4-acetonide

: 81939-86-8
trans,cis-3,5-dimethyl-1-phenylthio-trans,cis,cis-2,3,4-trihydroxycyclohexane 3,4-acetonide

Guidance literature:: Multi-step reaction with 2 steps

1: 95 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 0 - 20 °C

2: 97 percent / NaH / dimethylformamide / 24 h / 140 °C

With sodium hydride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00137a018

Reference yield:

: 81939-75-5,81939-76-6
5-methyl-6-(trimethylsiloxy)cyclohex-2-en-1-one

: 81939-86-8
trans,cis-3,5-dimethyl-1-phenylthio-trans,cis,cis-2,3,4-trihydroxycyclohexane 3,4-acetonide

Guidance literature:: Multi-step reaction with 5 steps

1: 2.) H₂O / 1.) (C₂H₅)2O, -78 deg C

2: H₂O, trifluoroacetic acid / tetrahydrofuran / 2 h / Ambient temperature

3: 45 percent / p-toluenesulfonic acid / 2 h / Ambient temperature

4: 95 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 0 - 20 °C

5: 97 percent / NaH / dimethylformamide / 24 h / 140 °C

With water; sodium hydride; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00137a018