(1R,2S,6Z)-2-(tert-butyldimethylsiloxy)-6-(2-hydroxyethylidene)-1-[(trimethylsilyl)methyl]cyclohexanol

Base Information

Chemical Name:(1R,2S,6Z)-2-(tert-butyldimethylsiloxy)-6-(2-hydroxyethylidene)-1-[(trimethylsilyl)methyl]cyclohexanol
CAS No.:603126-92-7
Molecular Formula:C₁₈H₃₈O₃Si₂
Molecular Weight:358.669
Hs Code.:

Synonyms:(1R,2S,6Z)-2-(tert-butyldimethylsiloxy)-6-(2-hydroxyethylidene)-1-[(trimethylsilyl)methyl]cyclohexanol

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Chemical Property of (1R,2S,6Z)-2-(tert-butyldimethylsiloxy)-6-(2-hydroxyethylidene)-1-[(trimethylsilyl)methyl]cyclohexanol

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Technology Process of (1R,2S,6Z)-2-(tert-butyldimethylsiloxy)-6-(2-hydroxyethylidene)-1-[(trimethylsilyl)methyl]cyclohexanol

There total 5 articles about (1R,2S,6Z)-2-(tert-butyldimethylsiloxy)-6-(2-hydroxyethylidene)-1-[(trimethylsilyl)methyl]cyclohexanol 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: 89.0%

: 603126-91-6
(7S,7aR)-7-(tert-butyldimethylsilyloxy)-7a-[(trimethylsilyl)methyl]-5,6,7,7a-tetrahydrobenzofuran-2(4H)-one

: 603126-92-7
(1R,2S,6Z)-2-(tert-butyldimethylsiloxy)-6-(2-hydroxyethylidene)-1-[(trimethylsilyl)methyl]cyclohexanol

Guidance literature:: (7S,7aR)-7-(tert-butyldimethylsilyloxy)-7a-[(trimethylsilyl)methyl]-5,6,7,7a-tetrahydrobenzofuran-2(4H)-one; With diisobutylaluminium hydride; at -78 - -42 ℃; for 1h;

With sodium tetrahydroborate; In methanol; for 16h;
DOI:10.1016/S0040-4039(02)02824-1

Reference yield:

: 108153-93-1
7-oxo-4,5,6,7-tetrahydrobenzofuran

: 603126-92-7
(1R,2S,6Z)-2-(tert-butyldimethylsiloxy)-6-(2-hydroxyethylidene)-1-[(trimethylsilyl)methyl]cyclohexanol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 91 percent / HCO2H; NEt3 / (R)-RuCl[(1S,2S)-p-TsNCH(C6H5)CH(C6H5)NH2](η⁶-p-cymene) / 144 h

2.1: 81 percent / imidazole / 16 h

3.1: 87 percent / CH₃CO₃H; NaOAc / CH₂Cl₂ / 6.5 h

4.1: 76 percent / CeCl₃ / 2 h / -78 - -42 °C

5.1: DIBAL / 1 h / -78 - -42 °C

5.2: 89 percent / NaBH₄ / methanol / 16 h

With 1H-imidazole; peracetic acid; formic acid; cerium(III) chloride; sodium acetate; diisobutylaluminium hydride; triethylamine; [(1S,2S)-N-(p-toluensulfonyl)-1,2-diphenylethanediamine](p-cymene)ruthenium (I); In dichloromethane;
DOI:10.1016/S0040-4039(02)02824-1

Reference yield:

: 603126-88-1
(7S)-4,5,6,7-tetrahydro-1-benzofuran-7-ol

: 603126-92-7
(1R,2S,6Z)-2-(tert-butyldimethylsiloxy)-6-(2-hydroxyethylidene)-1-[(trimethylsilyl)methyl]cyclohexanol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 81 percent / imidazole / 16 h

2.1: 87 percent / CH₃CO₃H; NaOAc / CH₂Cl₂ / 6.5 h

3.1: 76 percent / CeCl₃ / 2 h / -78 - -42 °C

4.1: DIBAL / 1 h / -78 - -42 °C

4.2: 89 percent / NaBH₄ / methanol / 16 h

With 1H-imidazole; peracetic acid; cerium(III) chloride; sodium acetate; diisobutylaluminium hydride; In dichloromethane;
DOI:10.1016/S0040-4039(02)02824-1