(3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-4-ethylcyclohexanone

Base Information

Chemical Name:(3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-4-ethylcyclohexanone
CAS No.:1447920-38-8
Molecular Formula:C₂₀H₄₂O₃Si₂
Molecular Weight:386.723
Hs Code.:

Synonyms:(3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-4-ethylcyclohexanone

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Chemical Property of (3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-4-ethylcyclohexanone

Chemical Property:

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Technology Process of (3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-4-ethylcyclohexanone

There total 9 articles about (3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-4-ethylcyclohexanone 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: 90.0%

: (3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-4-ethyl-1-(hydroxymethyl)cyclohexanol

: 1447920-38-8
(3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-4-ethylcyclohexanone

Guidance literature:: With sodium periodate; In methanol; water; at 0 - 20 ℃; for 2.16667h; Inert atmosphere;
DOI:10.1002/ejoc.201201261

Reference yield:

: 135711-62-5
methyl quinicate

: 1447920-38-8
(3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-4-ethylcyclohexanone

Guidance literature:: Multi-step reaction with 9 steps

1.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 3.17 h / 20 °C / Inert atmosphere

2.1: toluene; tetrahydrofuran / 2.5 h / -78 - 20 °C / Inert atmosphere

2.2: -78 - 0 °C / Inert atmosphere

3.1: sodium tetrahydroborate / methanol / 0 - 20 °C / Inert atmosphere

4.1: pyridinium p-toluenesulfonate / dichloromethane / 22 h / 40 °C / Inert atmosphere

5.1: borane-THF / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

5.2: 1 h / 0 - 20 °C / Inert atmosphere

6.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.17 h / 20 °C / Inert atmosphere

7.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -50 - -10 °C / Inert atmosphere

7.2: 2.08 h / -30 - 20 °C / Inert atmosphere

8.1: 10 wt% Pd(OH)2 on carbon; hydrogen / dichloromethane; ethanol / 2 h / 760.05 Torr

9.1: sodium periodate / methanol; water / 2.17 h / 0 - 20 °C / Inert atmosphere

With sodium tetrahydroborate; sodium periodate; n-butyllithium; borane-THF; 10 wt% Pd(OH)2 on carbon; hydrogen; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; toluene; 7.1: |Wittig Olefination / 7.2: |Wittig Olefination;
DOI:10.1002/ejoc.201201261

Reference yield:

: 213250-58-9
(3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-1-hydroxy-4-oxocyclohexanecarboxylic acid methyl ester

: 1447920-38-8
(3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-4-ethylcyclohexanone

Guidance literature:: Multi-step reaction with 8 steps

1.1: toluene; tetrahydrofuran / 2.5 h / -78 - 20 °C / Inert atmosphere

1.2: -78 - 0 °C / Inert atmosphere

2.1: sodium tetrahydroborate / methanol / 0 - 20 °C / Inert atmosphere

3.1: pyridinium p-toluenesulfonate / dichloromethane / 22 h / 40 °C / Inert atmosphere

4.1: borane-THF / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

4.2: 1 h / 0 - 20 °C / Inert atmosphere

5.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.17 h / 20 °C / Inert atmosphere

6.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -50 - -10 °C / Inert atmosphere

6.2: 2.08 h / -30 - 20 °C / Inert atmosphere

7.1: 10 wt% Pd(OH)2 on carbon; hydrogen / dichloromethane; ethanol / 2 h / 760.05 Torr

8.1: sodium periodate / methanol; water / 2.17 h / 0 - 20 °C / Inert atmosphere

With sodium tetrahydroborate; sodium periodate; n-butyllithium; borane-THF; 10 wt% Pd(OH)2 on carbon; hydrogen; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; toluene; 6.1: |Wittig Olefination / 6.2: |Wittig Olefination;
DOI:10.1002/ejoc.201201261