(2Z,6Z,10Z,14Z)-9-(benzenesulfonyl)-1-(tert-butyldiphenylsilyloxy)-16-chloro-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraene

Base Information

Chemical Name:(2Z,6Z,10Z,14Z)-9-(benzenesulfonyl)-1-(tert-butyldiphenylsilyloxy)-16-chloro-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraene
CAS No.:1056289-79-2
Molecular Formula:C₄₂H₅₅ClO₃SSi
Molecular Weight:703.501
Hs Code.:

Synonyms:(2Z,6Z,10Z,14Z)-9-(benzenesulfonyl)-1-(tert-butyldiphenylsilyloxy)-16-chloro-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraene

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Chemical Property of (2Z,6Z,10Z,14Z)-9-(benzenesulfonyl)-1-(tert-butyldiphenylsilyloxy)-16-chloro-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraene

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Technology Process of (2Z,6Z,10Z,14Z)-9-(benzenesulfonyl)-1-(tert-butyldiphenylsilyloxy)-16-chloro-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraene

There total 20 articles about (2Z,6Z,10Z,14Z)-9-(benzenesulfonyl)-1-(tert-butyldiphenylsilyloxy)-16-chloro-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraene 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: 91.0%

: 53343-13-8
1-hydroxypropan-2-one tetrahydropyran ether

: 1528749-24-7
C₄₁H₄₆OPSi⁽¹⁺⁾*I^(1-)

: 1056289-79-2
(2Z,6Z,10Z,14Z)-9-(benzenesulfonyl)-1-(tert-butyldiphenylsilyloxy)-16-chloro-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraene

Guidance literature:: C₄₁H₄₆OPSi⁽¹⁺⁾*I^(1-); With n-butyllithium; In tetrahydrofuran; hexane; for 1h;

1-hydroxypropan-2-one tetrahydropyran ether; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 16h; Inert atmosphere;
DOI:10.1021/ja409409h

Reference yield: 80.0%

: 1528749-27-0
(2Z,6Z,10Z,14Z)-8-(benzenesulfonyl)-16-[(tert-butyldiphenylsilyl)oxy]-2,6,10,14-tetramethylhexadeca-2,6,10,14-tetraen-1-ol

: 1056289-79-2
(2Z,6Z,10Z,14Z)-9-(benzenesulfonyl)-1-(tert-butyldiphenylsilyloxy)-16-chloro-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraene

Guidance literature:: With methanesulfonyl chloride; lithium chloride; In N,N-dimethyl-formamide; at -3 - 0 ℃; for 2h;
DOI:10.1021/ja409409h

Reference yield:

: 139109-03-8
(Z)-1-[(tert-butyldiphenylsilyl)oxy]-3,7-dimethyl-2,6-octadiene

: 1056289-79-2
(2Z,6Z,10Z,14Z)-9-(benzenesulfonyl)-1-(tert-butyldiphenylsilyloxy)-16-chloro-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraene

Guidance literature:: Multi-step reaction with 13 steps

1.1: N-Bromosuccinimide; water / tetrahydrofuran / 6 h / 0 °C

2.1: potassium carbonate / methanol / 16 h / 20 °C

3.1: periodic acid / 1,4-dioxane; water / 12 h / 0 °C

4.1: sodium tetrahydroborate; ethanol / 3 h / 0 °C

5.1: pyridine / 3 h / 20 °C

6.1: sodium iodide / acetone / 16 h / Reflux; Inert atmosphere

7.1: toluene / 20 h / Inert atmosphere; Reflux

8.1: n-butyllithium / tetrahydrofuran; hexane / 1 h

8.2: 16 h / -78 - 20 °C / Inert atmosphere

9.1: toluene-4-sulfonic acid / isopropyl alcohol; diethyl ether / 20 °C

10.1: methanesulfonyl chloride; lithium chloride / N,N-dimethyl-formamide / 2 h / -3 °C

11.1: n-butyllithium; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / tetrahydrofuran; hexane / 2 h / -78 °C

11.2: 3.5 h / -78 - -30 °C / Inert atmosphere

12.1: toluene-4-sulfonic acid / isopropyl alcohol; diethyl ether / 20 °C

13.1: methanesulfonyl chloride; lithium chloride / N,N-dimethyl-formamide / 2 h / -3 - 0 °C

With pyridine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium tetrahydroborate; N-Bromosuccinimide; n-butyllithium; ethanol; water; potassium carbonate; toluene-4-sulfonic acid; methanesulfonyl chloride; periodic acid; sodium iodide; lithium chloride; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; hexane; water; N,N-dimethyl-formamide; isopropyl alcohol; acetone; toluene;
DOI:10.1021/ja409409h