(5R,7S)-2,2,3,3,9,9,10,10-octamethyl-5-((S)-oxiran-2-ylmethyl)-7-(4-phenylbutyl)-4,8-dioxa-3,9-disilaundecane

Base Information

Chemical Name:(5R,7S)-2,2,3,3,9,9,10,10-octamethyl-5-((S)-oxiran-2-ylmethyl)-7-(4-phenylbutyl)-4,8-dioxa-3,9-disilaundecane
CAS No.:1351993-07-1
Molecular Formula:C₂₈H₅₂O₃Si₂
Molecular Weight:492.89
Hs Code.:

Synonyms:(5R,7S)-2,2,3,3,9,9,10,10-octamethyl-5-((S)-oxiran-2-ylmethyl)-7-(4-phenylbutyl)-4,8-dioxa-3,9-disilaundecane

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Chemical Property of (5R,7S)-2,2,3,3,9,9,10,10-octamethyl-5-((S)-oxiran-2-ylmethyl)-7-(4-phenylbutyl)-4,8-dioxa-3,9-disilaundecane

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Technology Process of (5R,7S)-2,2,3,3,9,9,10,10-octamethyl-5-((S)-oxiran-2-ylmethyl)-7-(4-phenylbutyl)-4,8-dioxa-3,9-disilaundecane

There total 14 articles about (5R,7S)-2,2,3,3,9,9,10,10-octamethyl-5-((S)-oxiran-2-ylmethyl)-7-(4-phenylbutyl)-4,8-dioxa-3,9-disilaundecane 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: 80.0%

: 1351993-06-0
(2S,4R,6S)-4,6-bis(tert-butyldimethylsilyloxy)-10-phenyldecane-1,2-diol

: 1351993-07-1
(5R,7S)-2,2,3,3,9,9,10,10-octamethyl-5-((S)-oxiran-2-ylmethyl)-7-(4-phenylbutyl)-4,8-dioxa-3,9-disilaundecane

Guidance literature:: (2S,4R,6S)-4,6-bis(tert-butyldimethylsilyloxy)-10-phenyldecane-1,2-diol; With di(n-butyl)tin oxide; triethylamine; p-toluenesulfonyl chloride; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere;

With potassium carbonate; In methanol; Inert atmosphere;
DOI:10.1016/j.tetasy.2011.09.017

Reference yield:

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

: 1351993-07-1
(5R,7S)-2,2,3,3,9,9,10,10-octamethyl-5-((S)-oxiran-2-ylmethyl)-7-(4-phenylbutyl)-4,8-dioxa-3,9-disilaundecane

Guidance literature:: Multi-step reaction with 11 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

With 1H-imidazole; sodium tetrahydroborate; palladium 10% on activated carbon; hydrogen; diisobutylaluminium hydride; di(n-butyl)tin oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; p-toluenesulfonyl chloride; D-Prolin; lithium chloride; In 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

: 1351993-07-1
(5R,7S)-2,2,3,3,9,9,10,10-octamethyl-5-((S)-oxiran-2-ylmethyl)-7-(4-phenylbutyl)-4,8-dioxa-3,9-disilaundecane

Guidance literature:: Multi-step reaction with 10 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

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