(1R,3S,5R)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-8,8-dimethyl-1-((E)-4-oxo-pent-2-enyl)-2,9-dioxa-bicyclo[3.3.1]nonan-7-one

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Chemical Name:(1R,3S,5R)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-8,8-dimethyl-1-((E)-4-oxo-pent-2-enyl)-2,9-dioxa-bicyclo[3.3.1]nonan-7-one
CAS No.:794587-11-4
Molecular Formula:C₃₂H₄₂O₅Si
Molecular Weight:534.768
Hs Code.:

Synonyms:(1R,3S,5R)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-8,8-dimethyl-1-((E)-4-oxo-pent-2-enyl)-2,9-dioxa-bicyclo[3.3.1]nonan-7-one

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Chemical Property of (1R,3S,5R)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-8,8-dimethyl-1-((E)-4-oxo-pent-2-enyl)-2,9-dioxa-bicyclo[3.3.1]nonan-7-one

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Technology Process of (1R,3S,5R)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-8,8-dimethyl-1-((E)-4-oxo-pent-2-enyl)-2,9-dioxa-bicyclo[3.3.1]nonan-7-one

There total 10 articles about (1R,3S,5R)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-8,8-dimethyl-1-((E)-4-oxo-pent-2-enyl)-2,9-dioxa-bicyclo[3.3.1]nonan-7-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: 75.0%

: 1067-71-6
Diethyl (2-oxopropyl)phosphonate

: 794587-09-0
{(1R,3S,5R)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-8,8-dimethyl-7-oxo-2,9-dioxa-bicyclo[3.3.1]non-1-yl}-acetic acid ethyl ester

: 794587-11-4
(1R,3S,5R)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-8,8-dimethyl-1-((E)-4-oxo-pent-2-enyl)-2,9-dioxa-bicyclo[3.3.1]nonan-7-one

Guidance literature:: {(1R,3S,5R)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-8,8-dimethyl-7-oxo-2,9-dioxa-bicyclo[3.3.1]non-1-yl}-acetic acid ethyl ester; With diisobutylaluminium hydride; In dichloromethane; toluene; at -90 ℃; for 0.5h;

Diethyl (2-oxopropyl)phosphonate; With sodium hydride; In tetrahydrofuran; dichloromethane; toluene; for 0.166667h; Heating;
DOI:10.1021/ol0483044

Reference yield:

: 66248-79-1
ethyl 4,4-dimethyl-3-oxo-hex-5-enoate

: 794587-11-4
(1R,3S,5R)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-8,8-dimethyl-1-((E)-4-oxo-pent-2-enyl)-2,9-dioxa-bicyclo[3.3.1]nonan-7-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: 72 percent / i-Pr₂NEt / acetonitrile; methanol; hexane / 24 h / 20 °C

2.1: 87 percent / camphorsulfonic acid / benzene / 1 h / Heating

3.1: 93 percent / (PCy₃)2Cl₂Ru=CHPh / CH₂Cl₂ / 11 h / 20 °C

4.1: 2-methyl-2-butene; BH₃ / tetrahydrofuran / 3 h / 0 °C

4.2: 91 percent / NaBO₃*4H₂O / tetrahydrofuran; H₂O / 1 h / 20 °C

5.1: 99 percent / imidazole / dimethylformamide / 2 h / 20 °C

6.1: 97 percent / citric acid monohydrate; OsO₄; N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; H₂O / 8 h / 20 °C

7.1: 80 percent / oxalyl chloride; DMSO; i-Pr₂NEt / CH₂Cl₂ / 1.5 h / -78 - 20 °C

8.1: 74 percent / SmI₂; HMPA / tetrahydrofuran; methanol / 0.17 h / 0 °C

9.1: DIBALH / CH₂Cl₂; toluene / 0.5 h / -90 °C

9.2: 75 percent / NaH / CH₂Cl₂; toluene; tetrahydrofuran / 0.17 h / Heating

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; osmium(VIII) oxide; samarium diiodide; 2-methyl-but-2-ene; oxalyl dichloride; camphor-10-sulfonic acid; borane; diisobutylaluminium hydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; citric acid; Grubbs catalyst first generation; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; benzene; 6.1: Sharpless dihydroxylation / 7.1: Swern oxidation / 9.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/ol0483044

Reference yield:

: (3R,5R)-hepta-1,6-diene-3,5-diol

: 794587-11-4
(1R,3S,5R)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-8,8-dimethyl-1-((E)-4-oxo-pent-2-enyl)-2,9-dioxa-bicyclo[3.3.1]nonan-7-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: 87 percent / camphorsulfonic acid / benzene / 1 h / Heating

2.1: 93 percent / (PCy₃)2Cl₂Ru=CHPh / CH₂Cl₂ / 11 h / 20 °C

3.1: 2-methyl-2-butene; BH₃ / tetrahydrofuran / 3 h / 0 °C

3.2: 91 percent / NaBO₃*4H₂O / tetrahydrofuran; H₂O / 1 h / 20 °C

4.1: 99 percent / imidazole / dimethylformamide / 2 h / 20 °C

5.1: 97 percent / citric acid monohydrate; OsO₄; N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; H₂O / 8 h / 20 °C

6.1: 80 percent / oxalyl chloride; DMSO; i-Pr₂NEt / CH₂Cl₂ / 1.5 h / -78 - 20 °C

7.1: 74 percent / SmI₂; HMPA / tetrahydrofuran; methanol / 0.17 h / 0 °C

8.1: DIBALH / CH₂Cl₂; toluene / 0.5 h / -90 °C

8.2: 75 percent / NaH / CH₂Cl₂; toluene; tetrahydrofuran / 0.17 h / Heating

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; osmium(VIII) oxide; samarium diiodide; 2-methyl-but-2-ene; oxalyl dichloride; camphor-10-sulfonic acid; borane; diisobutylaluminium hydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; citric acid; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; benzene; 5.1: Sharpless dihydroxylation / 6.1: Swern oxidation / 8.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/ol0483044