[(5S,6S)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,3-dienyl]-methanol

Base Information

Chemical Name:[(5S,6S)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,3-dienyl]-methanol
CAS No.:439213-17-9
Molecular Formula:C₁₉H₃₈O₃Si₂
Molecular Weight:370.68
Hs Code.:

Synonyms:[(5S,6S)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,3-dienyl]-methanol

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Chemical Property of [(5S,6S)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,3-dienyl]-methanol

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Technology Process of [(5S,6S)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,3-dienyl]-methanol

There total 2 articles about [(5S,6S)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,3-dienyl]-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: 88.0%

: 439290-17-2
methyl (S,S)-5,6-bis(tert-butyldimethylsilanyloxy)cyclohexa-1,3-dienecarboxylate

: 439213-17-9
[(5S,6S)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,3-dienyl]-methanol

Guidance literature:: With diisobutylaluminium hydride; In hexane; at 0 ℃; for 3h;
DOI:10.1039/b110420a

Reference yield:

: 176487-06-2
(2S,3S)-(+)-trans-2,3-dihydroxy-2,3-dihydrobenzoic acid

: 439213-17-9
[(5S,6S)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,3-dienyl]-methanol

Guidance literature:: Multi-step reaction with 3 steps

1: 81 percent / hexane; methanol / 6 h / 20 °C

2: 95 percent / NEt₃ / CH₂Cl₂ / 2 h / 20 °C

3: 88 percent / DIBAL-H / hexane / 3 h / 0 °C

With diisobutylaluminium hydride; triethylamine; In methanol; hexane; dichloromethane;
DOI:10.1039/b110420a

Reference yield:

: 439213-17-9
[(5S,6S)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,3-dienyl]-methanol

: 439290-20-7
benzoic acid 5,6-dihydroxy-3,8-dioxatricyclo[5.1.0.0^2,4]oct-4-ylmethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 91 percent / meta-chloroperoxybenzoic acid; NaHCO₃ / CH₂Cl₂ / 3 h / 20 °C

2: 82 percent / meta-chloroperoxybenzoic acid; NaHCO₃ / CH₂Cl₂ / 16 h / 50 °C

3: 73 percent / pyridine / 6 h / -5 °C

4: 64 percent / TBAF / tetrahydrofuran / 2 h / -78 - 20 °C

With pyridine; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1039/b110420a