[(4S,5R,6S)-4,5,6-Tris-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enyl]-methanol

Base Information

Chemical Name:[(4S,5R,6S)-4,5,6-Tris-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enyl]-methanol
CAS No.:134593-88-7
Molecular Formula:C₂₅H₅₄O₄Si₃
Molecular Weight:502.958
Hs Code.:

Synonyms:[(4S,5R,6S)-4,5,6-Tris-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enyl]-methanol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of [(4S,5R,6S)-4,5,6-Tris-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enyl]-methanol

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Technology Process of [(4S,5R,6S)-4,5,6-Tris-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enyl]-methanol

There total 5 articles about [(4S,5R,6S)-4,5,6-Tris-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enyl]-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: 99.0%

: 134593-87-6
(4R,5S,6R)-4,5,6-Tris-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enecarboxylic acid methyl ester

: 134593-88-7
[(4S,5R,6S)-4,5,6-Tris-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enyl]-methanol

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

Reference yield:

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

: 134593-88-7
[(4S,5R,6S)-4,5,6-Tris-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enyl]-methanol

Guidance literature:: Multi-step reaction with 5 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

With 2,6-dimethylpyridine; dmap; 2,2'-azobis(isobutyronitrile); 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

: 134593-88-7
[(4S,5R,6S)-4,5,6-Tris-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enyl]-methanol

Guidance literature:: Multi-step reaction with 3 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

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