(2R,4R,5S,6S)-4-((3S,5S,6R,7S)-6-(tert-butyldimethylsilyloxy)-8-(4-methoxybenzyloxy)-3,5,7-trimethyloctyl)-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-((3S,5S,6R,7S)-6-(tert-butyldimethylsilyloxy)-8-(4-methoxybenzyloxy)-3,5,7-trimethyloctyl)-2-(4-methoxyphenyl)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-5-methyl-1,3-dioxane
CAS No.:1185750-59-7
Molecular Formula:C₅₆H₈₄O₇Si₂
Molecular Weight:925.45
Hs Code.:

(2R,4R,5S,6S)-4-((3S,5S,6R,7S)-6-(tert-butyldimethylsilyloxy)-8-(4-methoxybenzyloxy)-3,5,7-trimethyloctyl)-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-((3S,5S,6R,7S)-6-(tert-butyldimethylsilyloxy)-8-(4-methoxybenzyloxy)-3,5,7-trimethyloctyl)-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-((3S,5S,6R,7S)-6-(tert-butyldimethylsilyloxy)-8-(4-methoxybenzyloxy)-3,5,7-trimethyloctyl)-2-(4-methoxyphenyl)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-5-methyl-1,3-dioxane

There total 14 articles about (2R,4R,5S,6S)-4-((3S,5S,6R,7S)-6-(tert-butyldimethylsilyloxy)-8-(4-methoxybenzyloxy)-3,5,7-trimethyloctyl)-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:

: 1185750-46-2
(2S,3R,4S,6S)-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-trimethyloctan-3-ol

: 69739-34-0
t-butyldimethylsiyl triflate

: 1185750-59-7
(2R,4R,5S,6S)-4-((3S,5S,6R,7S)-6-(tert-butyldimethylsilyloxy)-8-(4-methoxybenzyloxy)-3,5,7-trimethyloctyl)-2-(4-methoxyphenyl)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-5-methyl-1,3-dioxane

: (2R,4R,5S,6S)-4-((3R,5S,6R,7S)-6-(tert-butyldimethylsilyloxy)-8-(4-methoxybenzyloxy)-3,5,7-trimethyloctyl)-2-(4-methoxyphenyl)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-5-methyl-1,3-dioxane

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 0.5h; optical yield given as %de; Inert atmosphere;
DOI:10.1016/j.tet.2009.04.073

Reference yield:

: 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

: 1185750-59-7
(2R,4R,5S,6S)-4-((3S,5S,6R,7S)-6-(tert-butyldimethylsilyloxy)-8-(4-methoxybenzyloxy)-3,5,7-trimethyloctyl)-2-(4-methoxyphenyl)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-5-methyl-1,3-dioxane

: (2R,4R,5S,6S)-4-((3R,5S,6R,7S)-6-(tert-butyldimethylsilyloxy)-8-(4-methoxybenzyloxy)-3,5,7-trimethyloctyl)-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: triisopropoxytitanium(IV) chloride; cyclopentylmagnesium chloride / diethyl ether; hexane; toluene / 2 h / -78 - -30 °C / Inert atmosphere

1.2: 2 h / -78 - -30 °C / Inert atmosphere

1.3: 24 h / 20 °C / Inert atmosphere

2.1: Ir(cycloocta-1,5-diene)(C₁₀H₁₅C₃H₃NOC₂H₄N₂C₃H₂(C₆H₃(iPr)2) tetrakis(3,5-bis(trifluoromethyl)phenyl)borate; hydrogen / dichloromethane / 4 h / 25 °C / 38787.1 Torr / Molecular sieve

3.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

With 2,6-dimethylpyridine; triisopropoxytitanium(IV) chloride; Ir(cycloocta-1,5-diene)(C₁₀H₁₅C₃H₃NOC₂H₄N₂C₃H₂(C₆H₃(iPr)2) tetrakis(3,5-bis(trifluoromethyl)phenyl)borate; hydrogen; cyclopentylmagnesium chloride; In diethyl ether; hexane; dichloromethane; toluene;
DOI:10.1016/j.tet.2009.04.073

Reference yield:

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

: 1185750-59-7
(2R,4R,5S,6S)-4-((3S,5S,6R,7S)-6-(tert-butyldimethylsilyloxy)-8-(4-methoxybenzyloxy)-3,5,7-trimethyloctyl)-2-(4-methoxyphenyl)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-5-methyl-1,3-dioxane

: (2R,4R,5S,6S)-4-((3R,5S,6R,7S)-6-(tert-butyldimethylsilyloxy)-8-(4-methoxybenzyloxy)-3,5,7-trimethyloctyl)-2-(4-methoxyphenyl)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-5-methyl-1,3-dioxane

Guidance literature:: Multi-step reaction with 5 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

4.1: Ir(cycloocta-1,5-diene)(C₁₀H₁₅C₃H₃NOC₂H₄N₂C₃H₂(C₆H₃(iPr)2) tetrakis(3,5-bis(trifluoromethyl)phenyl)borate; hydrogen / dichloromethane / 4 h / 25 °C / 38787.1 Torr / Molecular sieve

5.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

With 2,6-dimethylpyridine; triisopropoxytitanium(IV) chloride; Ir(cycloocta-1,5-diene)(C₁₀H₁₅C₃H₃NOC₂H₄N₂C₃H₂(C₆H₃(iPr)2) tetrakis(3,5-bis(trifluoromethyl)phenyl)borate; hydrogen; cyclopentylmagnesium chloride; magnesium bromide ethyl etherate; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene;
DOI:10.1016/j.tet.2009.04.073