(5E,9E)-(3R,4R,7S,8S)-11-allyloxy-1-(tert-butyldiphenylsilanyloxy)-8-ethyl-3-methoxymethoxy-4-(2-trityloxyethyl)-undeca-5,9-diene-4,7-diol

Base Information

Chemical Name:(5E,9E)-(3R,4R,7S,8S)-11-allyloxy-1-(tert-butyldiphenylsilanyloxy)-8-ethyl-3-methoxymethoxy-4-(2-trityloxyethyl)-undeca-5,9-diene-4,7-diol
CAS No.:1120309-38-7
Molecular Formula:C₅₅H₆₈O₇Si
Molecular Weight:869.226
Hs Code.:

Synonyms:(5E,9E)-(3R,4R,7S,8S)-11-allyloxy-1-(tert-butyldiphenylsilanyloxy)-8-ethyl-3-methoxymethoxy-4-(2-trityloxyethyl)-undeca-5,9-diene-4,7-diol

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Chemical Property of (5E,9E)-(3R,4R,7S,8S)-11-allyloxy-1-(tert-butyldiphenylsilanyloxy)-8-ethyl-3-methoxymethoxy-4-(2-trityloxyethyl)-undeca-5,9-diene-4,7-diol

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Technology Process of (5E,9E)-(3R,4R,7S,8S)-11-allyloxy-1-(tert-butyldiphenylsilanyloxy)-8-ethyl-3-methoxymethoxy-4-(2-trityloxyethyl)-undeca-5,9-diene-4,7-diol

There total 16 articles about (5E,9E)-(3R,4R,7S,8S)-11-allyloxy-1-(tert-butyldiphenylsilanyloxy)-8-ethyl-3-methoxymethoxy-4-(2-trityloxyethyl)-undeca-5,9-diene-4,7-diol 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: 62.0%

: (E)-(3R,7R,8S)-11-allyloxy-1-(tert-butyldiphenylsilanyloxy)-8-ethyl-3-methoxymethoxy-4-[2-(trityloxy)ethyl]undec-9-en-5-yne-4,7-diol

: 1120309-38-7
(5E,9E)-(3R,4R,7S,8S)-11-allyloxy-1-(tert-butyldiphenylsilanyloxy)-8-ethyl-3-methoxymethoxy-4-(2-trityloxyethyl)-undeca-5,9-diene-4,7-diol

Guidance literature:: With sodium bis(2-methoxyethoxy)aluminium dihydride; In diethyl ether; toluene; at 0 ℃; for 6h; stereoselective reaction;
DOI:10.1021/ol8029142

Reference yield: 62.0%

: 1120309-19-4
(E)-(3R,4R,7R,8S)-11-allyloxy-1-(tert-butyldiphenylsilyloxy)-8-ethyl-3-methoxymethoxy-4-[2-(trityloxy)ethyl]undec-9-en-5-yne-4,7-diol

: 1120309-38-7
(5E,9E)-(3R,4R,7S,8S)-11-allyloxy-1-(tert-butyldiphenylsilanyloxy)-8-ethyl-3-methoxymethoxy-4-(2-trityloxyethyl)-undeca-5,9-diene-4,7-diol

Guidance literature:: With sodium bis(2-methoxyethoxy)aluminium dihydride; In diethyl ether; toluene; at 0 ℃; for 6h;
DOI:10.1016/j.tet.2010.05.050

Reference yield:

: 1120309-29-6
2-(allyloxy)-N-methoxy-N-methylacetamide

: 1120309-38-7
(5E,9E)-(3R,4R,7S,8S)-11-allyloxy-1-(tert-butyldiphenylsilanyloxy)-8-ethyl-3-methoxymethoxy-4-(2-trityloxyethyl)-undeca-5,9-diene-4,7-diol

Guidance literature:: Multi-step reaction with 8 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 - 0 °C

1.2: -78 - -40 °C

2.1: (1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II); isopropyl alcohol / 0.75 h / 20 °C

3.1: copper(I) bromide; lithium bromide; zinc / tetrahydrofuran; ethylene dibromide; isopropyl alcohol / 18 h / 20 °C / Reflux

4.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C

5.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C

7.1: isopropylmagnesium chloride / tetrahydrofuran; diethyl ether / -20 - 0 °C

7.2: 1.5 h / -20 °C

8.1: sodium bis(2-methoxyethoxy)aluminium dihydride / diethyl ether; toluene / 6 h / 0 °C

With (1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II); n-butyllithium; potassium tert-butylate; tetrabutyl ammonium fluoride; isopropylmagnesium chloride; sodium bis(2-methoxyethoxy)aluminium dihydride; isopropyl alcohol; copper(I) bromide; lithium bromide; zinc; In tetrahydrofuran; diethyl ether; hexane; ethylene dibromide; isopropyl alcohol; toluene; 5.1: [2,3]-Wittig rearrangement;
DOI:10.1021/ol8029142