(2R,4R)-10-Allyl-8-bromo-7-(tert-butyl-diphenyl-silanyloxymethyl)-2,4-dimethyl-1,5-dioxa-spiro[5.5]undeca-7,10-dien-9-one

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Chemical Name:(2R,4R)-10-Allyl-8-bromo-7-(tert-butyl-diphenyl-silanyloxymethyl)-2,4-dimethyl-1,5-dioxa-spiro[5.5]undeca-7,10-dien-9-one
CAS No.:532393-21-8
Molecular Formula:C₃₁H₃₇BrO₄Si
Molecular Weight:581.622
Hs Code.:

Synonyms:(2R,4R)-10-Allyl-8-bromo-7-(tert-butyl-diphenyl-silanyloxymethyl)-2,4-dimethyl-1,5-dioxa-spiro[5.5]undeca-7,10-dien-9-one

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Chemical Property of (2R,4R)-10-Allyl-8-bromo-7-(tert-butyl-diphenyl-silanyloxymethyl)-2,4-dimethyl-1,5-dioxa-spiro[5.5]undeca-7,10-dien-9-one

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Technology Process of (2R,4R)-10-Allyl-8-bromo-7-(tert-butyl-diphenyl-silanyloxymethyl)-2,4-dimethyl-1,5-dioxa-spiro[5.5]undeca-7,10-dien-9-one

There total 16 articles about (2R,4R)-10-Allyl-8-bromo-7-(tert-butyl-diphenyl-silanyloxymethyl)-2,4-dimethyl-1,5-dioxa-spiro[5.5]undeca-7,10-dien-9-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: 82.0%

: 42075-32-1
(2R,4R)-pentanediol

: 311312-51-3
2-bromo-3-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-4,4-dimethoxy-6-(2-propenyl)-2,5-cyclohexadien-1-one

: 532393-21-8
(2R,4R)-10-Allyl-8-bromo-7-(tert-butyl-diphenyl-silanyloxymethyl)-2,4-dimethyl-1,5-dioxa-spiro[5.5]undeca-7,10-dien-9-one

Guidance literature:: With pyridinium p-toluenesulfonate; In benzene; at 80 ℃; for 0.5h;
DOI:10.1021/ja021396c

Reference yield:

: 1194-98-5
2,5-Dihydroxybenzaldehyde

: 532393-21-8
(2R,4R)-10-Allyl-8-bromo-7-(tert-butyl-diphenyl-silanyloxymethyl)-2,4-dimethyl-1,5-dioxa-spiro[5.5]undeca-7,10-dien-9-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: Br₂ / CHCl₃ / 20 °C

2.1: 10.64 g / imidazole / CH₂Cl₂ / 0.25 h / 20 °C

3.1: NaH / tetrahydrofuran / 0.5 h

3.2: 72 percent / DMA / tetrahydrofuran / 6 h / 65 °C

4.1: 100 percent / NaBH₄ / ethanol / 0.5 h / 0 °C

5.1: 93 percent / imidazole / dimethylformamide / 2 h / 20 °C

6.1: TBAF / tetrahydrofuran / 0.17 h / 0 °C

7.1: K₂CO₃ / dimethylformamide / 2.5 h / 20 °C

8.1: 2 h / 180 °C

8.2: 70 percent / PhI(OAc)2 / 0.33 h / 20 °C

9.1: 82 percent / pyridinium p-toluenesulfonate / benzene / 0.5 h / 80 °C

With 1H-imidazole; sodium tetrahydroborate; tetrabutyl ammonium fluoride; bromine; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; In tetrahydrofuran; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; benzene; 8.1: Claisen rearrangement;
DOI:10.1021/ja021396c

Reference yield:

: 85432-87-7
2-bromo-3,6-dimethoxybenzaldehyde

: 532393-21-8
(2R,4R)-10-Allyl-8-bromo-7-(tert-butyl-diphenyl-silanyloxymethyl)-2,4-dimethyl-1,5-dioxa-spiro[5.5]undeca-7,10-dien-9-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 1.42 g / conc. H₂SO₄ / 14 h / 70 °C

2.1: 96 percent / K₂CO₃ / dimethylformamide / 3 h

3.1: NaBH₄ / ethanol / 0.5 h / 20 °C

4.1: 94 percent / imidazole / dimethylformamide / 2.5 h / 20 °C

5.1: 2 h / 180 °C

5.2: 70 percent / PhI(OAc)2 / 0.33 h / 20 °C

6.1: 82 percent / pyridinium p-toluenesulfonate / benzene / 0.5 h / 80 °C

With 1H-imidazole; sodium tetrahydroborate; sulfuric acid; pyridinium p-toluenesulfonate; potassium carbonate; In ethanol; N,N-dimethyl-formamide; benzene; 5.1: Claisen rearrangement;
DOI:10.1021/ja021396c