(2S,3R,4S,5E,7E)-8-((2R,4R,5S,6S)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-1-(4-methoxybenzyloxy)-2,4,6-trimethylocta-5,7-dien-3-ol

Base Information

Chemical Name:(2S,3R,4S,5E,7E)-8-((2R,4R,5S,6S)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-1-(4-methoxybenzyloxy)-2,4,6-trimethylocta-5,7-dien-3-ol
CAS No.:1185750-44-0
Molecular Formula:C₅₀H₆₆O₇Si
Molecular Weight:807.155
Hs Code.:

(2S,3R,4S,5E,7E)-8-((2R,4R,5S,6S)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-1-(4-methoxybenzyloxy)-2,4,6-trimethylocta-5,7-dien-3-ol

Synonyms:(2S,3R,4S,5E,7E)-8-((2R,4R,5S,6S)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-1-(4-methoxybenzyloxy)-2,4,6-trimethylocta-5,7-dien-3-ol

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Chemical Property of (2S,3R,4S,5E,7E)-8-((2R,4R,5S,6S)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-1-(4-methoxybenzyloxy)-2,4,6-trimethylocta-5,7-dien-3-ol

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Technology Process of (2S,3R,4S,5E,7E)-8-((2R,4R,5S,6S)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-1-(4-methoxybenzyloxy)-2,4,6-trimethylocta-5,7-dien-3-ol

There total 11 articles about (2S,3R,4S,5E,7E)-8-((2R,4R,5S,6S)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-1-(4-methoxybenzyloxy)-2,4,6-trimethylocta-5,7-dien-3-ol 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: 63.0%

: 1185750-45-1
(4S,5R,6S)-7-(4-methoxybenzyloxy)-5-trimethylsilyloxy-4,6-dimethylhept-2-yne

: 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

: 1185750-44-0
(2S,3R,4S,5E,7E)-8-((2R,4R,5S,6S)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-1-(4-methoxybenzyloxy)-2,4,6-trimethylocta-5,7-dien-3-ol

Guidance literature:: (4S,5R,6S)-7-(4-methoxybenzyloxy)-5-trimethylsilyloxy-4,6-dimethylhept-2-yne; 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 -78 - -30 ℃; for 2h; Inert atmosphere;

With sodium methylate; In methanol; diethyl ether; hexane; toluene; at 20 ℃; for 24h; regioselective reaction; Inert atmosphere;
DOI:10.1016/j.tet.2009.04.073

Reference yield:

: 1158955-70-4
(2R,3S,4S)-5-(tert-butyldiphenylsilyloxy)-3-hydroxy-N-methoxy-N,2,4-trimethylpentanamide

: 1185750-44-0
(2S,3R,4S,5E,7E)-8-((2R,4R,5S,6S)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-1-(4-methoxybenzyloxy)-2,4,6-trimethylocta-5,7-dien-3-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: tetrahydrofuran / 4 h / -30 - 0 °C / Inert atmosphere

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

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

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

4.2: 2 h / -78 - -30 °C / Inert atmosphere

4.3: 24 h / 20 °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:

: M-(-)-2-(tributylstannyl)-2,3-pentadiene

: 1185750-44-0
(2S,3R,4S,5E,7E)-8-((2R,4R,5S,6S)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-1-(4-methoxybenzyloxy)-2,4,6-trimethylocta-5,7-dien-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: magnesium bromide ethyl etherate / dichloromethane / 18 h / -23 °C / Inert atmosphere

2.1: triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere

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

3.2: 2 h / -78 - -30 °C / Inert atmosphere

3.3: 24 h / 20 °C / Inert atmosphere

With triisopropoxytitanium(IV) chloride; cyclopentylmagnesium chloride; magnesium bromide ethyl etherate; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene;
DOI:10.1016/j.tet.2009.04.073