2-[(3S,4R,5S)-3,4,5-Tris-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-ethanol

Base Information

Chemical Name:2-[(3S,4R,5S)-3,4,5-Tris-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-ethanol
CAS No.:134593-90-1
Molecular Formula:C₂₇H₅₆O₄Si₃
Molecular Weight:528.996
Hs Code.:

Synonyms:2-[(3S,4R,5S)-3,4,5-Tris-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-ethanol

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Chemical Property of 2-[(3S,4R,5S)-3,4,5-Tris-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-ethanol

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Technology Process of 2-[(3S,4R,5S)-3,4,5-Tris-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-ethanol

There total 7 articles about 2-[(3S,4R,5S)-3,4,5-Tris-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-ethanol 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: 92.0%

: 134593-89-8,134678-34-5
[(3S,4R,5S)-3,4,5-Tris-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-acetic acid ethyl ester

: 134593-90-1
2-[(3S,4R,5S)-3,4,5-Tris-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-ethanol

Guidance literature:: With diisobutylaluminium hydride; In toluene; at -78 ℃; for 2.5h;
DOI:10.1021/jo00014a003

Reference yield:

: 19978-32-6
3-bromo-2H-pyran-2-one

: 134593-90-1
2-[(3S,4R,5S)-3,4,5-Tris-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-ethanol

Guidance literature:: Multi-step reaction with 7 steps

1: 63 percent / i-Pr₂NEt / CH₂Cl₂ / 4 h / 90 °C

2: 98 percent / p-TsOH / 17 h

3: 100 percent / 4-DMAP, 2,6-lutidine / CH₂Cl₂

4: 1.) Bu3SnH, AIBN 2.) DBU / 1.) PhH, Δ 2.) CH2Cl2, 25 deg C

5: 99 percent / DIBAL-H / toluene / -78 °C

6: 1.) 2,4,6-trimethylbenzoic acid, 2.) 9-fluorenone / 1.) CH₂Cl₂, 150 deg C, 3 h, 2.) t-BuOMe, irradiation

7: 92 percent / DIBAL-H / toluene / 2.5 h / -78 °C

With 2,6-dimethylpyridine; dmap; 9-fluorenone; 2,2'-azobis(isobutyronitrile); mesitylenecarboxylic acid; tri-n-butyl-tin hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; In dichloromethane; toluene;
DOI:10.1021/jo00014a003

Reference yield:

: 134593-85-4
(1R,4R,5S,6S)-1-Bromo-4,5,6-trihydroxy-cyclohex-2-enecarboxylic acid methyl ester

: 134593-90-1
2-[(3S,4R,5S)-3,4,5-Tris-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-ethanol

Guidance literature:: Multi-step reaction with 5 steps

1: 100 percent / 4-DMAP, 2,6-lutidine / CH₂Cl₂

2: 1.) Bu3SnH, AIBN 2.) DBU / 1.) PhH, Δ 2.) CH2Cl2, 25 deg C

3: 99 percent / DIBAL-H / toluene / -78 °C

4: 1.) 2,4,6-trimethylbenzoic acid, 2.) 9-fluorenone / 1.) CH₂Cl₂, 150 deg C, 3 h, 2.) t-BuOMe, irradiation

5: 92 percent / DIBAL-H / toluene / 2.5 h / -78 °C

With 2,6-dimethylpyridine; dmap; 9-fluorenone; 2,2'-azobis(isobutyronitrile); mesitylenecarboxylic acid; tri-n-butyl-tin hydride; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; toluene;
DOI:10.1021/jo00014a003