3-[(1R,2R)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-methyl-2-triethylsilanyloxymethyl-1-((Z)-1-trimethylsilanyloxy-penta-1,4-dienyl)-cyclohex-3-enyl]-propionitrile

Base Information

Chemical Name:3-[(1R,2R)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-methyl-2-triethylsilanyloxymethyl-1-((Z)-1-trimethylsilanyloxy-penta-1,4-dienyl)-cyclohex-3-enyl]-propionitrile
CAS No.:1027430-18-7
Molecular Formula:C₃₀H₅₃NO₄Si₂
Molecular Weight:547.926
Hs Code.:

3-[(1R,2R)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-methyl-2-triethylsilanyloxymethyl-1-((Z)-1-trimethylsilanyloxy-penta-1,4-dienyl)-cyclohex-3-enyl]-propionitrile

Synonyms:3-[(1R,2R)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-methyl-2-triethylsilanyloxymethyl-1-((Z)-1-trimethylsilanyloxy-penta-1,4-dienyl)-cyclohex-3-enyl]-propionitrile

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Chemical Property of 3-[(1R,2R)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-methyl-2-triethylsilanyloxymethyl-1-((Z)-1-trimethylsilanyloxy-penta-1,4-dienyl)-cyclohex-3-enyl]-propionitrile

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Technology Process of 3-[(1R,2R)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-methyl-2-triethylsilanyloxymethyl-1-((Z)-1-trimethylsilanyloxy-penta-1,4-dienyl)-cyclohex-3-enyl]-propionitrile

There total 11 articles about 3-[(1R,2R)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-methyl-2-triethylsilanyloxymethyl-1-((Z)-1-trimethylsilanyloxy-penta-1,4-dienyl)-cyclohex-3-enyl]-propionitrile 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:

: 75-77-4
chloro-trimethyl-silane

: 917-57-7
vinyllithium

: 645394-06-5
(1'R,2'R,4''R)-3-[1'-acryloyl-4'-(2'',2''-dimethyl-[1'',3'']dioxolan-4''-yl)-3'-methyl-2'-triethylsilanyloxymethylcyclohex-3'-enyl]propionitrile

: 1027430-18-7
3-[(1R,2R)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-methyl-2-triethylsilanyloxymethyl-1-((Z)-1-trimethylsilanyloxy-penta-1,4-dienyl)-cyclohex-3-enyl]-propionitrile

Guidance literature:: vinyllithium; (1'R,2'R,4''R)-3-[1'-acryloyl-4'-(2'',2''-dimethyl-[1'',3'']dioxolan-4''-yl)-3'-methyl-2'-triethylsilanyloxymethylcyclohex-3'-enyl]propionitrile; With 2-thienyl(cyano)copper lithium; In tetrahydrofuran; diethyl ether; at -78 ℃; for 1.5h;

chloro-trimethyl-silane; In tetrahydrofuran; diethyl ether; at -78 ℃; for 0.333333h;
DOI:10.1021/ol035939e

Reference yield:

: 133481-14-8
(2S)-2,3-O-isopropylidene-N-methoxy-N-methylpropanamide

: 1027430-18-7
3-[(1R,2R)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-methyl-2-triethylsilanyloxymethyl-1-((Z)-1-trimethylsilanyloxy-penta-1,4-dienyl)-cyclohex-3-enyl]-propionitrile

Guidance literature:: Multi-step reaction with 11 steps

1.1: n-BuLi / hexane; tetrahydrofuran / 1 h / -78 °C

1.2: 71 percent / tetrahydrofuran; hexane / 1.5 h / -78 °C

2.1: n-BuLi / hexane; tetrahydrofuran / -78 - 0 °C

2.2: 84 percent / hexane; tetrahydrofuran / -78 - 0 °C

3.1: glacial acetic acid / ethanol / 48 h / 20 °C

4.1: pH 7 buffer; DDQ / CH₂Cl₂ / 8 h / 20 °C

5.1: triethylamine / tetrahydrofuran / 0.67 h / -10 - 20 °C

6.1: 72 percent / NaBH₄ / methanol / 1 h / -35 °C

7.1: 88 percent / oxalyl chloride; dimethylsulfoxide; triethylamine / CH₂Cl₂ / -78 - 20 °C

8.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / 0 °C

8.2: tetrahydrofuran; hexane / 2 h / 0 - 20 °C

8.3: 48 mg / Mg / methanol / 6 h / 0 - 20 °C

9.1: 63 percent / diethyl ether / 1 h / -78 °C

10.1: 68 percent / pyridine / 10 h / 20 °C

11.1: 2-thienyl(cyano)copper lithium / tetrahydrofuran; diethyl ether / 1.5 h / -78 °C

11.2: tetrahydrofuran; diethyl ether / 0.33 h / -78 °C

With pyridine; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; 2-thienyl(cyano)copper lithium; pH 7 buffer; acetic acid; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; 2.2: Wittig reaction / 3.1: Diels-Alder reaction / 7.1: Swern oxidation / 8.2: Horner-Wadsworth-Emmons condensation;
DOI:10.1021/ol035939e

Reference yield:

: 645393-92-6
(4S)-(E)-1-(2,2-dimethyl-[1,3]dioxolan-4-yl)-4-(4-methoxybenzyloxy)-2-methylbut-2-en-1-one

: 1027430-18-7
3-[(1R,2R)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-methyl-2-triethylsilanyloxymethyl-1-((Z)-1-trimethylsilanyloxy-penta-1,4-dienyl)-cyclohex-3-enyl]-propionitrile

Guidance literature:: Multi-step reaction with 10 steps

1.1: n-BuLi / hexane; tetrahydrofuran / -78 - 0 °C

1.2: 84 percent / hexane; tetrahydrofuran / -78 - 0 °C

2.1: glacial acetic acid / ethanol / 48 h / 20 °C

3.1: pH 7 buffer; DDQ / CH₂Cl₂ / 8 h / 20 °C

4.1: triethylamine / tetrahydrofuran / 0.67 h / -10 - 20 °C

5.1: 72 percent / NaBH₄ / methanol / 1 h / -35 °C

6.1: 88 percent / oxalyl chloride; dimethylsulfoxide; triethylamine / CH₂Cl₂ / -78 - 20 °C

7.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / 0 °C

7.2: tetrahydrofuran; hexane / 2 h / 0 - 20 °C

7.3: 48 mg / Mg / methanol / 6 h / 0 - 20 °C

8.1: 63 percent / diethyl ether / 1 h / -78 °C

9.1: 68 percent / pyridine / 10 h / 20 °C

10.1: 2-thienyl(cyano)copper lithium / tetrahydrofuran; diethyl ether / 1.5 h / -78 °C

10.2: tetrahydrofuran; diethyl ether / 0.33 h / -78 °C

With pyridine; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; 2-thienyl(cyano)copper lithium; pH 7 buffer; acetic acid; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; 1.2: Wittig reaction / 2.1: Diels-Alder reaction / 6.1: Swern oxidation / 7.2: Horner-Wadsworth-Emmons condensation;
DOI:10.1021/ol035939e