(2R,4R,5S,6S)-4-((1E,3E,5S,6R,7S)-8-(benzyloxy)-6-triethylsilyloxy-3,5,7-trimethylocta-1,3-dienyl)-2-(4-methoxyphenyl)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-5-methyl-1,3-dioxane

Base Information

Chemical Name:(2R,4R,5S,6S)-4-((1E,3E,5S,6R,7S)-8-(benzyloxy)-6-triethylsilyloxy-3,5,7-trimethylocta-1,3-dienyl)-2-(4-methoxyphenyl)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-5-methyl-1,3-dioxane
CAS No.:1185750-54-2
Molecular Formula:C₅₅H₇₈O₆Si₂
Molecular Weight:891.392
Hs Code.:

(2R,4R,5S,6S)-4-((1E,3E,5S,6R,7S)-8-(benzyloxy)-6-triethylsilyloxy-3,5,7-trimethylocta-1,3-dienyl)-2-(4-methoxyphenyl)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-5-methyl-1,3-dioxane

Synonyms:(2R,4R,5S,6S)-4-((1E,3E,5S,6R,7S)-8-(benzyloxy)-6-triethylsilyloxy-3,5,7-trimethylocta-1,3-dienyl)-2-(4-methoxyphenyl)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-5-methyl-1,3-dioxane

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Chemical Property of (2R,4R,5S,6S)-4-((1E,3E,5S,6R,7S)-8-(benzyloxy)-6-triethylsilyloxy-3,5,7-trimethylocta-1,3-dienyl)-2-(4-methoxyphenyl)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-5-methyl-1,3-dioxane

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Technology Process of (2R,4R,5S,6S)-4-((1E,3E,5S,6R,7S)-8-(benzyloxy)-6-triethylsilyloxy-3,5,7-trimethylocta-1,3-dienyl)-2-(4-methoxyphenyl)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-5-methyl-1,3-dioxane

There total 8 articles about (2R,4R,5S,6S)-4-((1E,3E,5S,6R,7S)-8-(benzyloxy)-6-triethylsilyloxy-3,5,7-trimethylocta-1,3-dienyl)-2-(4-methoxyphenyl)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-5-methyl-1,3-dioxane 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: 66.0%

: 1022186-63-5
(2S,3R,4S)-1-(benzyloxy)-2,4-dimethyl-3-(triethylsilanyloxy)-5-heptyne

: 1185750-29-1
(2S,4S,5R,6S)-4-ethynyl-2-(4-methoxyphenyl)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-5-methyl-1,3-dioxane

: 1185750-54-2
(2R,4R,5S,6S)-4-((1E,3E,5S,6R,7S)-8-(benzyloxy)-6-triethylsilyloxy-3,5,7-trimethylocta-1,3-dienyl)-2-(4-methoxyphenyl)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-5-methyl-1,3-dioxane

Guidance literature:: (2S,3R,4S)-1-(benzyloxy)-2,4-dimethyl-3-(triethylsilanyloxy)-5-heptyne; With triisopropoxytitanium(IV) chloride; cyclopentylmagnesium chloride; In diethyl ether; hexane; toluene; at -78 - -30 ℃; for 2h; Inert atmosphere;

(2S,4S,5R,6S)-4-ethynyl-2-(4-methoxyphenyl)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-5-methyl-1,3-dioxane; In diethyl ether; hexane; toluene; at -30 ℃; for 2h; regioselective reaction; Inert atmosphere;
DOI:10.1016/j.tet.2009.04.073

Reference yield:

: 1185750-31-5
(4R,5S,6S)-7-(tert-butyldiphenylsilyloxy)-5-hydroxy-4,6-dimethylhept-1-yn-3-one

: 1185750-54-2
(2R,4R,5S,6S)-4-((1E,3E,5S,6R,7S)-8-(benzyloxy)-6-triethylsilyloxy-3,5,7-trimethylocta-1,3-dienyl)-2-(4-methoxyphenyl)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-5-methyl-1,3-dioxane

Guidance literature:: Multi-step reaction with 3 steps

1.1: diisobutylaluminium hydride / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

2.1: pyridinium p-toluenesulfonate / dichloromethane / Inert atmosphere; Reflux

3.1: triisopropoxytitanium(IV) chloride; cyclopentylmagnesium chloride / diethyl ether; hexane; toluene / 2 h / -78 - -30 °C / Inert atmosphere

3.2: 2 h / -30 °C / Inert atmosphere

With triisopropoxytitanium(IV) chloride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; cyclopentylmagnesium chloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene;
DOI:10.1016/j.tet.2009.04.073

Reference yield:

: 1185750-53-1
(3S,4R,5S,6S)-7-(tert-butyldiphenylsilyloxy)-4,6-dimethylhept-1-yne-3,5-diol

: 1185750-54-2
(2R,4R,5S,6S)-4-((1E,3E,5S,6R,7S)-8-(benzyloxy)-6-triethylsilyloxy-3,5,7-trimethylocta-1,3-dienyl)-2-(4-methoxyphenyl)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-5-methyl-1,3-dioxane

Guidance literature:: Multi-step reaction with 2 steps

1.1: pyridinium p-toluenesulfonate / dichloromethane / Inert atmosphere; Reflux

2.1: triisopropoxytitanium(IV) chloride; cyclopentylmagnesium chloride / diethyl ether; hexane; toluene / 2 h / -78 - -30 °C / Inert atmosphere

2.2: 2 h / -30 °C / Inert atmosphere

With triisopropoxytitanium(IV) chloride; pyridinium p-toluenesulfonate; cyclopentylmagnesium chloride; In diethyl ether; hexane; dichloromethane; toluene;
DOI:10.1016/j.tet.2009.04.073