(2S,3R,4S,5E,7E)-1-(benzyloxy)-8-((2R,4R,5S,6S)-6-((S,Z)-hexa-3,5-dien-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-2,4,6-trimethylocta-5,7-dien-3-ol

Base Information

Chemical Name:(2S,3R,4S,5E,7E)-1-(benzyloxy)-8-((2R,4R,5S,6S)-6-((S,Z)-hexa-3,5-dien-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-2,4,6-trimethylocta-5,7-dien-3-ol
CAS No.:1185750-21-3
Molecular Formula:C₃₆H₄₈O₅
Molecular Weight:560.774
Hs Code.:

(2S,3R,4S,5E,7E)-1-(benzyloxy)-8-((2R,4R,5S,6S)-6-((S,Z)-hexa-3,5-dien-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-2,4,6-trimethylocta-5,7-dien-3-ol

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Chemical Property of (2S,3R,4S,5E,7E)-1-(benzyloxy)-8-((2R,4R,5S,6S)-6-((S,Z)-hexa-3,5-dien-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-2,4,6-trimethylocta-5,7-dien-3-ol

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Technology Process of (2S,3R,4S,5E,7E)-1-(benzyloxy)-8-((2R,4R,5S,6S)-6-((S,Z)-hexa-3,5-dien-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-2,4,6-trimethylocta-5,7-dien-3-ol

There total 9 articles about (2S,3R,4S,5E,7E)-1-(benzyloxy)-8-((2R,4R,5S,6S)-6-((S,Z)-hexa-3,5-dien-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-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:

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

: 1185750-22-4
(2S,4S,5R,6S)-4-ethynyl-6-((S,Z)-hexa-3,5-dien-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxane

: C₃₆H₄₈O₅

: 1185750-21-3
(2S,3R,4S,5E,7E)-1-(benzyloxy)-8-((2R,4R,5S,6S)-6-((S,Z)-hexa-3,5-dien-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-2,4,6-trimethylocta-5,7-dien-3-ol

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-6-((S,Z)-hexa-3,5-dien-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxane; In diethyl ether; hexane; toluene; at -30 ℃; for 2h; Inert atmosphere;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; regioselective reaction; Inert atmosphere;
DOI:10.1016/j.tet.2009.04.073

Reference yield:

: 1185750-51-9
tert-butyl((S)-2-((2S,4S,5R,6S)-2-(4-methoxyphenyl)-5-methyl-6-((trimethylsilyl)ethynyl)-1,3-dioxan-4-yl)propoxy)diphenylsilane

: C₃₆H₄₈O₅

: 1185750-21-3
(2S,3R,4S,5E,7E)-1-(benzyloxy)-8-((2R,4R,5S,6S)-6-((S,Z)-hexa-3,5-dien-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-2,4,6-trimethylocta-5,7-dien-3-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / -78 - 20 °C / Inert atmosphere

3.1: toluene / -78 - 20 °C / Inert atmosphere; Molecular sieve

3.2: 2 h / 0 - 20 °C / Inert atmosphere

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

4.2: 2 h / -30 °C / Inert atmosphere

4.3: 20 °C / Inert atmosphere

With triisopropoxytitanium(IV) chloride; oxalyl dichloride; tetrabutyl ammonium fluoride; cyclopentylmagnesium chloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene;
DOI:10.1016/j.tet.2009.04.073

Reference yield:

: C₁₇H₂₀O₄

: C₃₆H₄₈O₅

: 1185750-21-3
(2S,3R,4S,5E,7E)-1-(benzyloxy)-8-((2R,4R,5S,6S)-6-((S,Z)-hexa-3,5-dien-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-2,4,6-trimethylocta-5,7-dien-3-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: toluene / -78 - 20 °C / Inert atmosphere; Molecular sieve

1.2: 2 h / 0 - 20 °C / Inert atmosphere

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

2.3: 20 °C / Inert atmosphere

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