(2S,4S,6S,8R,9S)-4-(tert-Butyl-diphenyl-silanyloxy)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undecane-2-carboxylic acid methyl ester

Base Information

Chemical Name:(2S,4S,6S,8R,9S)-4-(tert-Butyl-diphenyl-silanyloxy)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undecane-2-carboxylic acid methyl ester
CAS No.:105087-23-8
Molecular Formula:C₂₉H₄₀O₅Si
Molecular Weight:496.719
Hs Code.:

Synonyms:(2S,4S,6S,8R,9S)-4-(tert-Butyl-diphenyl-silanyloxy)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undecane-2-carboxylic acid methyl ester

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Chemical Property of (2S,4S,6S,8R,9S)-4-(tert-Butyl-diphenyl-silanyloxy)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undecane-2-carboxylic acid methyl ester

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Technology Process of (2S,4S,6S,8R,9S)-4-(tert-Butyl-diphenyl-silanyloxy)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undecane-2-carboxylic acid methyl ester

There total 15 articles about (2S,4S,6S,8R,9S)-4-(tert-Butyl-diphenyl-silanyloxy)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undecane-2-carboxylic acid methyl ester 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:

: 2436-90-0
(S)-(+)-dihydromyrcene

: 105087-23-8
(2S,4S,6S,8R,9S)-4-(tert-Butyl-diphenyl-silanyloxy)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undecane-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 1.) ozone, 2.) Me₂S / 1.) CH₂Cl₂, -78 degC, 1.5 h, 2.) CH₂Cl₂, from -78 deg C to RT

2: CrO₃, aq. H₂SO₄ / acetone / 0 - 10 °C

3: 85 percent / I₂ / acetonitrile / 1.) -25 deg C, 10 h, 2.) 0 deg C, 4 h

4: 90 percent / Bu₃SnH / benzene / 2 h / Heating

5: 1.) LDA / 1.) THF, a) -78 deg C, 10 min, b) 0 deg C, 1 h, 2.) THF, a) -78 deg C, 15 min, b) 0 deg C, 1 h

6: TsOH*H₂O / CH₂Cl₂ / 0.5 h

7: 58 percent / H₂ / 5percent Rh/Al / ethanol / 2 h

8: 30 percent / LDA / tetrahydrofuran / 4 h / -78 °C

9: 87 percent / pyridinium chlorochromate / CH₂Cl₂ / 4 h / Heating

10: 77 percent / NaBH₄ / 1,2-dimethoxy-ethane / 1 h / -20 °C

11: imidazole / dimethylformamide / 1 h / Ambient temperature

With 1H-imidazole; chromium(VI) oxide; sodium tetrahydroborate; dimethylsulfide; sulfuric acid; hydrogen; iodine; tri-n-butyl-tin hydride; toluene-4-sulfonic acid; ozone; pyridinium chlorochromate; lithium diisopropyl amide; rhodium on aluminium; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile; benzene;
DOI:10.1021/jo00375a017

Reference yield:

: 69274-86-8
(S)-(+)-4-methylhex-5-enoic acid

: 105087-23-8
(2S,4S,6S,8R,9S)-4-(tert-Butyl-diphenyl-silanyloxy)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undecane-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 85 percent / I₂ / acetonitrile / 1.) -25 deg C, 10 h, 2.) 0 deg C, 4 h

2: 90 percent / Bu₃SnH / benzene / 2 h / Heating

3: 1.) LDA / 1.) THF, a) -78 deg C, 10 min, b) 0 deg C, 1 h, 2.) THF, a) -78 deg C, 15 min, b) 0 deg C, 1 h

4: TsOH*H₂O / CH₂Cl₂ / 0.5 h

5: 58 percent / H₂ / 5percent Rh/Al / ethanol / 2 h

6: 30 percent / LDA / tetrahydrofuran / 4 h / -78 °C

7: 87 percent / pyridinium chlorochromate / CH₂Cl₂ / 4 h / Heating

8: 77 percent / NaBH₄ / 1,2-dimethoxy-ethane / 1 h / -20 °C

9: imidazole / dimethylformamide / 1 h / Ambient temperature

With 1H-imidazole; sodium tetrahydroborate; hydrogen; iodine; tri-n-butyl-tin hydride; toluene-4-sulfonic acid; pyridinium chlorochromate; lithium diisopropyl amide; rhodium on aluminium; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1021/jo00375a017

Reference yield:

: 82467-25-2
(+)-(5S,6R)-tetrahydro-5,6-dimethyl-2H-pyran-2-one

: 105087-23-8
(2S,4S,6S,8R,9S)-4-(tert-Butyl-diphenyl-silanyloxy)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undecane-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) LDA / 1.) THF, a) -78 deg C, 10 min, b) 0 deg C, 1 h, 2.) THF, a) -78 deg C, 15 min, b) 0 deg C, 1 h

2: TsOH*H₂O / CH₂Cl₂ / 0.5 h

3: 58 percent / H₂ / 5percent Rh/Al / ethanol / 2 h

4: 30 percent / LDA / tetrahydrofuran / 4 h / -78 °C

5: 87 percent / pyridinium chlorochromate / CH₂Cl₂ / 4 h / Heating

6: 77 percent / NaBH₄ / 1,2-dimethoxy-ethane / 1 h / -20 °C

7: imidazole / dimethylformamide / 1 h / Ambient temperature

With 1H-imidazole; sodium tetrahydroborate; hydrogen; toluene-4-sulfonic acid; pyridinium chlorochromate; lithium diisopropyl amide; rhodium on aluminium; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00375a017