(5R,9S,10R,12S,13S,E)-5-((4R,5R)-5-cyclohexyl-2,2-dimethyl-1,3-dioxolan-4-yl)-3,3-diethyl-5,9,12,13,15,15,16,16-octamethyl-10-(triethylsilyloxy)-4,14-dioxa-3,15-disilaheptadec-6-ene

Base Information

Chemical Name:(5R,9S,10R,12S,13S,E)-5-((4R,5R)-5-cyclohexyl-2,2-dimethyl-1,3-dioxolan-4-yl)-3,3-diethyl-5,9,12,13,15,15,16,16-octamethyl-10-(triethylsilyloxy)-4,14-dioxa-3,15-disilaheptadec-6-ene
CAS No.:1181635-71-1
Molecular Formula:C₄₂H₈₆O₅Si₃
Molecular Weight:755.398
Hs Code.:

(5R,9S,10R,12S,13S,E)-5-((4R,5R)-5-cyclohexyl-2,2-dimethyl-1,3-dioxolan-4-yl)-3,3-diethyl-5,9,12,13,15,15,16,16-octamethyl-10-(triethylsilyloxy)-4,14-dioxa-3,15-disilaheptadec-6-ene

Synonyms:(5R,9S,10R,12S,13S,E)-5-((4R,5R)-5-cyclohexyl-2,2-dimethyl-1,3-dioxolan-4-yl)-3,3-diethyl-5,9,12,13,15,15,16,16-octamethyl-10-(triethylsilyloxy)-4,14-dioxa-3,15-disilaheptadec-6-ene

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Chemical Property of (5R,9S,10R,12S,13S,E)-5-((4R,5R)-5-cyclohexyl-2,2-dimethyl-1,3-dioxolan-4-yl)-3,3-diethyl-5,9,12,13,15,15,16,16-octamethyl-10-(triethylsilyloxy)-4,14-dioxa-3,15-disilaheptadec-6-ene

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Technology Process of (5R,9S,10R,12S,13S,E)-5-((4R,5R)-5-cyclohexyl-2,2-dimethyl-1,3-dioxolan-4-yl)-3,3-diethyl-5,9,12,13,15,15,16,16-octamethyl-10-(triethylsilyloxy)-4,14-dioxa-3,15-disilaheptadec-6-ene

There total 30 articles about (5R,9S,10R,12S,13S,E)-5-((4R,5R)-5-cyclohexyl-2,2-dimethyl-1,3-dioxolan-4-yl)-3,3-diethyl-5,9,12,13,15,15,16,16-octamethyl-10-(triethylsilyloxy)-4,14-dioxa-3,15-disilaheptadec-6-ene 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: 29.0%

: 1181635-73-3
(S)-2-((4R,5R)-5-cyclohexyl-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(triethylsilyloxy)propanal

: 1181635-75-5
5-((3S,4R,6S,7S)-7-(tert-butyldimethylsilyloxy)-3,6-dimethyl-4-(triethylsilyloxy)octylsulfonyl)-1-phenyl-1H-tetrazole

: (5R,9S,10R,12S,13S,Z)-5-((4R,5R)-5-cyclohexyl-2,2-dimethyl-1,3-dioxolan-4-yl)-3,3-diethyl-5,9,12,13,15,15,16,16-octamethyl-10-(triethylsilyloxy)-4,14-dioxa-3,15-disilaheptadec-6-ene

: 1181635-71-1
(5R,9S,10R,12S,13S,E)-5-((4R,5R)-5-cyclohexyl-2,2-dimethyl-1,3-dioxolan-4-yl)-3,3-diethyl-5,9,12,13,15,15,16,16-octamethyl-10-(triethylsilyloxy)-4,14-dioxa-3,15-disilaheptadec-6-ene

Guidance literature:: 5-((3S,4R,6S,7S)-7-(tert-butyldimethylsilyloxy)-3,6-dimethyl-4-(triethylsilyloxy)octylsulfonyl)-1-phenyl-1H-tetrazole; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 0.583333h; Inert atmosphere;

(S)-2-((4R,5R)-5-cyclohexyl-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(triethylsilyloxy)propanal; In tetrahydrofuran; toluene; at -78 - 25 ℃; optical yield given as %de; Inert atmosphere;
DOI:10.1021/ol901480s

Reference yield: 27.0%

: 1181635-73-3
(S)-2-((4R,5R)-5-cyclohexyl-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(triethylsilyloxy)propanal

: 1181635-75-5
5-((3S,4R,6S,7S)-7-(tert-butyldimethylsilyloxy)-3,6-dimethyl-4-(triethylsilyloxy)octylsulfonyl)-1-phenyl-1H-tetrazole

: 1181635-71-1
(5R,9S,10R,12S,13S,E)-5-((4R,5R)-5-cyclohexyl-2,2-dimethyl-1,3-dioxolan-4-yl)-3,3-diethyl-5,9,12,13,15,15,16,16-octamethyl-10-(triethylsilyloxy)-4,14-dioxa-3,15-disilaheptadec-6-ene

Guidance literature:: 5-((3S,4R,6S,7S)-7-(tert-butyldimethylsilyloxy)-3,6-dimethyl-4-(triethylsilyloxy)octylsulfonyl)-1-phenyl-1H-tetrazole; With potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃; Inert atmosphere;

(S)-2-((4R,5R)-5-cyclohexyl-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(triethylsilyloxy)propanal; In tetrahydrofuran; at -78 - 25 ℃; optical yield given as %de; Inert atmosphere;
DOI:10.1021/ol901480s

Reference yield:

: 1181635-76-6
1-[(4R,5R)-5-cyclohexyl-2,2-dimethyl-1,3-dioxolan-4-yl]ethanone

: 1181635-71-1
(5R,9S,10R,12S,13S,E)-5-((4R,5R)-5-cyclohexyl-2,2-dimethyl-1,3-dioxolan-4-yl)-3,3-diethyl-5,9,12,13,15,15,16,16-octamethyl-10-(triethylsilyloxy)-4,14-dioxa-3,15-disilaheptadec-6-ene

Guidance literature:: Multi-step reaction with 4 steps

1.1: iodine; magnesium / tetrahydrofuran / Reflux; Inert atmosphere

1.2: 0 °C / Inert atmosphere

2.1: 2,6-dimethylpyridine / dichloromethane / 1 h / -78 °C

3.1: oxygen; ozone / dichloromethane / -78 °C

3.2: -78 - 25 °C

4.1: potassium hexamethylsilazane / tetrahydrofuran / -78 °C / Inert atmosphere

4.2: -78 - 25 °C / Inert atmosphere

With 2,6-dimethylpyridine; iodine; oxygen; potassium hexamethylsilazane; ozone; magnesium; In tetrahydrofuran; dichloromethane; 4.1: Julia-Kocienski olefination / 4.2: Julia-Kocienski olefination;
DOI:10.1021/ol901480s