(1S,2R,3S)-1,2,3-Tris-(tert-butyl-dimethyl-silanyloxy)-5-[2-chloro-eth-(Z)-ylidene]-4-methylene-cyclohexane

Base Information

Chemical Name:(1S,2R,3S)-1,2,3-Tris-(tert-butyl-dimethyl-silanyloxy)-5-[2-chloro-eth-(Z)-ylidene]-4-methylene-cyclohexane
CAS No.:134593-91-2
Molecular Formula:C₂₇H₅₅ClO₃Si₃
Molecular Weight:547.441
Hs Code.:

Synonyms:(1S,2R,3S)-1,2,3-Tris-(tert-butyl-dimethyl-silanyloxy)-5-[2-chloro-eth-(Z)-ylidene]-4-methylene-cyclohexane

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Chemical Property of (1S,2R,3S)-1,2,3-Tris-(tert-butyl-dimethyl-silanyloxy)-5-[2-chloro-eth-(Z)-ylidene]-4-methylene-cyclohexane

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Technology Process of (1S,2R,3S)-1,2,3-Tris-(tert-butyl-dimethyl-silanyloxy)-5-[2-chloro-eth-(Z)-ylidene]-4-methylene-cyclohexane

There total 8 articles about (1S,2R,3S)-1,2,3-Tris-(tert-butyl-dimethyl-silanyloxy)-5-[2-chloro-eth-(Z)-ylidene]-4-methylene-cyclohexane 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%

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

: 134593-91-2
(1S,2R,3S)-1,2,3-Tris-(tert-butyl-dimethyl-silanyloxy)-5-[2-chloro-eth-(Z)-ylidene]-4-methylene-cyclohexane

Guidance literature:: With N-chloro-succinimide; dimethylsulfide;
DOI:10.1021/jo00014a003

Reference yield:

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

: 134593-91-2
(1S,2R,3S)-1,2,3-Tris-(tert-butyl-dimethyl-silanyloxy)-5-[2-chloro-eth-(Z)-ylidene]-4-methylene-cyclohexane

Guidance literature:: Multi-step reaction with 8 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

8: 97 percent / NCS, Me₂S

With 2,6-dimethylpyridine; dmap; N-chloro-succinimide; 9-fluorenone; dimethylsulfide; 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

: 134593-91-2
(1S,2R,3S)-1,2,3-Tris-(tert-butyl-dimethyl-silanyloxy)-5-[2-chloro-eth-(Z)-ylidene]-4-methylene-cyclohexane

Guidance literature:: Multi-step reaction with 6 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

6: 97 percent / NCS, Me₂S

With 2,6-dimethylpyridine; dmap; N-chloro-succinimide; 9-fluorenone; dimethylsulfide; 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