(R)-6-((2R,4S)-2,4-bis(tert-butyldimethylsilyloxy)-8-phenyloctyl)-5,6-dihydro-2H-pyran-2-one

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Chemical Name:(R)-6-((2R,4S)-2,4-bis(tert-butyldimethylsilyloxy)-8-phenyloctyl)-5,6-dihydro-2H-pyran-2-one
CAS No.:1351993-10-6
Molecular Formula:C₃₁H₅₄O₄Si₂
Molecular Weight:546.938
Hs Code.:

Synonyms:(R)-6-((2R,4S)-2,4-bis(tert-butyldimethylsilyloxy)-8-phenyloctyl)-5,6-dihydro-2H-pyran-2-one

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Chemical Property of (R)-6-((2R,4S)-2,4-bis(tert-butyldimethylsilyloxy)-8-phenyloctyl)-5,6-dihydro-2H-pyran-2-one

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Technology Process of (R)-6-((2R,4S)-2,4-bis(tert-butyldimethylsilyloxy)-8-phenyloctyl)-5,6-dihydro-2H-pyran-2-one

There total 16 articles about (R)-6-((2R,4S)-2,4-bis(tert-butyldimethylsilyloxy)-8-phenyloctyl)-5,6-dihydro-2H-pyran-2-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: 88.0%

: 1351993-09-3
(4R,6R,8S)-6,8-bis(tert-butyldimethylsilyloxy)-12-phenyldodec-1-en-4-yl acrylate

: 1351993-10-6
(R)-6-((2R,4S)-2,4-bis(tert-butyldimethylsilyloxy)-8-phenyloctyl)-5,6-dihydro-2H-pyran-2-one

Guidance literature:: With Grubbs catalyst first generation; In dichloromethane; for 12h; Reflux; Inert atmosphere;
DOI:10.1016/j.tetasy.2011.09.017

Reference yield:

: 1351993-02-6
(S)-methyl 4-hydroxy-8-phenyloctanoate

: 1351993-10-6
(R)-6-((2R,4S)-2,4-bis(tert-butyldimethylsilyloxy)-8-phenyloctyl)-5,6-dihydro-2H-pyran-2-one

Guidance literature:: Multi-step reaction with 14 steps

1.1: 1H-imidazole / dichloromethane / 0 - 20 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / dichloromethane / -78 °C / Inert atmosphere

3.1: D-Prolin / dimethyl sulfoxide / 1 h / 25 °C / Inert atmosphere

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / dimethyl sulfoxide / 1 h / 0 - 20 °C / Inert atmosphere

5.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 8 h

6.1: 1H-imidazole / dichloromethane / 0 - 20 °C / Inert atmosphere

7.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / 0 - 20 °C / Inert atmosphere

8.1: D-Prolin / dimethyl sulfoxide / 1 h / 25 °C / Inert atmosphere

9.1: sodium tetrahydroborate / methanol; dimethyl sulfoxide / 0.17 h / 0 °C / Inert atmosphere

10.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 12 h / 760.05 Torr

11.1: di(n-butyl)tin oxide; triethylamine; p-toluenesulfonyl chloride / dichloromethane / 2 h / 20 °C / Inert atmosphere

11.2: Inert atmosphere

12.1: copper(l) iodide / tetrahydrofuran / 12 h / -20 °C / Inert atmosphere

12.2: Saturated solution; Inert atmosphere

13.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / -78 - 20 °C / Inert atmosphere

14.1: Grubbs catalyst first generation / dichloromethane / 12 h / Reflux; Inert atmosphere

With 1H-imidazole; Grubbs catalyst first generation; sodium tetrahydroborate; copper(l) iodide; palladium 10% on activated carbon; hydrogen; diisobutylaluminium hydride; di(n-butyl)tin oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; p-toluenesulfonyl chloride; D-Prolin; lithium chloride; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; toluene; 4.1: Horner-Wadsworth-Emmons olefination;
DOI:10.1016/j.tetasy.2011.09.017

Reference yield:

: 1351993-03-7
(S)-methyl 4-(tert-butyldimethylsilyloxy)-8-phenyloctanoate

: 1351993-10-6
(R)-6-((2R,4S)-2,4-bis(tert-butyldimethylsilyloxy)-8-phenyloctyl)-5,6-dihydro-2H-pyran-2-one

Guidance literature:: Multi-step reaction with 13 steps

1.1: diisobutylaluminium hydride / dichloromethane / -78 °C / Inert atmosphere

2.1: D-Prolin / dimethyl sulfoxide / 1 h / 25 °C / Inert atmosphere

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / dimethyl sulfoxide / 1 h / 0 - 20 °C / Inert atmosphere

4.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 8 h

5.1: 1H-imidazole / dichloromethane / 0 - 20 °C / Inert atmosphere

6.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / 0 - 20 °C / Inert atmosphere

7.1: D-Prolin / dimethyl sulfoxide / 1 h / 25 °C / Inert atmosphere

8.1: sodium tetrahydroborate / methanol; dimethyl sulfoxide / 0.17 h / 0 °C / Inert atmosphere

9.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 12 h / 760.05 Torr

10.1: di(n-butyl)tin oxide; triethylamine; p-toluenesulfonyl chloride / dichloromethane / 2 h / 20 °C / Inert atmosphere

10.2: Inert atmosphere

11.1: copper(l) iodide / tetrahydrofuran / 12 h / -20 °C / Inert atmosphere

11.2: Saturated solution; Inert atmosphere

12.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / -78 - 20 °C / Inert atmosphere

13.1: Grubbs catalyst first generation / dichloromethane / 12 h / Reflux; Inert atmosphere

With 1H-imidazole; Grubbs catalyst first generation; sodium tetrahydroborate; copper(l) iodide; palladium 10% on activated carbon; hydrogen; diisobutylaluminium hydride; di(n-butyl)tin oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; p-toluenesulfonyl chloride; D-Prolin; lithium chloride; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; toluene; 3.1: Horner-Wadsworth-Emmons olefination;
DOI:10.1016/j.tetasy.2011.09.017