(2S,5R)-2-[(S)-2-(tert-butyldimethylsilyloxy)-1-methylethyl]-6-(1,3-dithian-2-ylidene)-5-methylcyclohexan-1-one

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Chemical Name:(2S,5R)-2-[(S)-2-(tert-butyldimethylsilyloxy)-1-methylethyl]-6-(1,3-dithian-2-ylidene)-5-methylcyclohexan-1-one
CAS No.:181698-23-7
Molecular Formula:C₂₀H₃₆O₂S₂Si
Molecular Weight:400.722
Hs Code.:

Synonyms:(2S,5R)-2-[(S)-2-(tert-butyldimethylsilyloxy)-1-methylethyl]-6-(1,3-dithian-2-ylidene)-5-methylcyclohexan-1-one

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Chemical Property of (2S,5R)-2-[(S)-2-(tert-butyldimethylsilyloxy)-1-methylethyl]-6-(1,3-dithian-2-ylidene)-5-methylcyclohexan-1-one

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Technology Process of (2S,5R)-2-[(S)-2-(tert-butyldimethylsilyloxy)-1-methylethyl]-6-(1,3-dithian-2-ylidene)-5-methylcyclohexan-1-one

There total 6 articles about (2S,5R)-2-[(S)-2-(tert-butyldimethylsilyloxy)-1-methylethyl]-6-(1,3-dithian-2-ylidene)-5-methylcyclohexan-1-one 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:

: 20549-46-6
(+)-neoisopulegol

: 181698-23-7
(2S,5R)-2-[(S)-2-(tert-butyldimethylsilyloxy)-1-methylethyl]-6-(1,3-dithian-2-ylidene)-5-methylcyclohexan-1-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 88 percent / t-BuOOH / VO(acac)2 / benzene / 20 °C

2.1: 79 percent / NaBH₃CN; BF₃*OEt₂; bromocresol green / tetrahydrofuran / 12 h / 20 °C

3.1: 84 percent / imidazole / dimethylformamide / 0.25 h / 20 °C

4.1: 88 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 3.5 h / -65 - 20 °C

5.1: LHMDS / tetrahydrofuran / 0.83 h / -85 °C

5.2: HMPA / tetrahydrofuran / 1.92 h / -85 - 0 °C

6.1: LHMDS / tetrahydrofuran; hexane / 0.5 h / -78 °C

6.2: 2.35 g / tetrahydrofuran; hexane / 13 h / -78 - 20 °C

With 1H-imidazole; tert.-butylhydroperoxide; oxalyl dichloride; boron trifluoride diethyl etherate; bromocresol green; sodium cyanoborohydride; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; bis(acetylacetonate)oxovanadium; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; benzene; 4.1: Swern oxidation;
DOI:10.1039/b102961b

Reference yield:

: 13834-16-7
(1R,2S,5R)-2-[(S)-2-hydroxy-1-methylethyl]-5-methylcyclohexan-1-ol

: 181698-23-7
(2S,5R)-2-[(S)-2-(tert-butyldimethylsilyloxy)-1-methylethyl]-6-(1,3-dithian-2-ylidene)-5-methylcyclohexan-1-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 84 percent / imidazole / dimethylformamide / 0.25 h / 20 °C

2.1: 88 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 3.5 h / -65 - 20 °C

3.1: LHMDS / tetrahydrofuran / 0.83 h / -85 °C

3.2: HMPA / tetrahydrofuran / 1.92 h / -85 - 0 °C

4.1: LHMDS / tetrahydrofuran; hexane / 0.5 h / -78 °C

4.2: 2.35 g / tetrahydrofuran; hexane / 13 h / -78 - 20 °C

With 1H-imidazole; oxalyl dichloride; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 2.1: Swern oxidation;
DOI:10.1039/b102961b

Reference yield:

: 109-64-8
1,3-dibromo-propane

: (3R,6S)-6-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-dimercaptomethylene-3-methyl-cyclohexanone

: 181698-23-7
(2S,5R)-2-[(S)-2-(tert-butyldimethylsilyloxy)-1-methylethyl]-6-(1,3-dithian-2-ylidene)-5-methylcyclohexan-1-one

Guidance literature:: (3R,6S)-6-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-dimercaptomethylene-3-methyl-cyclohexanone; With lithium hexamethyldisilazane; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

1,3-dibromo-propane; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 13h;
DOI:10.1039/b102961b