(2S,3R,4S,6S)-1-(benzyloxy)-8-((2R,4R,5S,6S)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-2,4,6-trimethyloctan-3-ol

Base Information

Chemical Name:(2S,3R,4S,6S)-1-(benzyloxy)-8-((2R,4R,5S,6S)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-2,4,6-trimethyloctan-3-ol
CAS No.:1185750-27-9
Molecular Formula:C₄₉H₆₈O₆Si
Molecular Weight:781.161
Hs Code.:

(2S,3R,4S,6S)-1-(benzyloxy)-8-((2R,4R,5S,6S)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-2,4,6-trimethyloctan-3-ol

Synonyms:(2S,3R,4S,6S)-1-(benzyloxy)-8-((2R,4R,5S,6S)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-2,4,6-trimethyloctan-3-ol

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Chemical Property of (2S,3R,4S,6S)-1-(benzyloxy)-8-((2R,4R,5S,6S)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-2,4,6-trimethyloctan-3-ol

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Technology Process of (2S,3R,4S,6S)-1-(benzyloxy)-8-((2R,4R,5S,6S)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-2,4,6-trimethyloctan-3-ol

There total 9 articles about (2S,3R,4S,6S)-1-(benzyloxy)-8-((2R,4R,5S,6S)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-2,4,6-trimethyloctan-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:

: 1185750-28-0
(2S,3R,4S,5E,7E)-1-(benzyloxy)-8-((2R,4R,5S,6S)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-2,4,6-trimethylocta-5,7-dien-3-ol

: 1185750-27-9
(2S,3R,4S,6S)-1-(benzyloxy)-8-((2R,4R,5S,6S)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-2,4,6-trimethyloctan-3-ol

: (2S,3R,4S,6R)-1-(benzyloxy)-8-((2R,4R,5S,6S)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-2,4,6-trimethyloctan-3-ol

Guidance literature:: With Ir(cycloocta-1,5-diene)(C₁₀H₁₅C₃H₃NOC₂H₄N₂C₃H₂(C₆H₃(iPr)2) tetrakis(3,5-bis(trifluoromethyl)phenyl)borate; hydrogen; In dichloromethane; at 25 ℃; for 4h; under 38787.1 Torr; optical yield given as %de; diastereoselective reaction;
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

: 1185750-27-9
(2S,3R,4S,6S)-1-(benzyloxy)-8-((2R,4R,5S,6S)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-2,4,6-trimethyloctan-3-ol

: (2S,3R,4S,6R)-1-(benzyloxy)-8-((2R,4R,5S,6S)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-2,4,6-trimethyloctan-3-ol

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 / -30 °C / Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere

3.1: 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

With triisopropoxytitanium(IV) chloride; Ir(cycloocta-1,5-diene)(C₁₀H₁₅C₃H₃NOC₂H₄N₂C₃H₂(C₆H₃(iPr)2) tetrakis(3,5-bis(trifluoromethyl)phenyl)borate; tetrabutyl ammonium fluoride; hydrogen; cyclopentylmagnesium chloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene;
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

: 1185750-27-9
(2S,3R,4S,6S)-1-(benzyloxy)-8-((2R,4R,5S,6S)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-2,4,6-trimethyloctan-3-ol

: (2S,3R,4S,6R)-1-(benzyloxy)-8-((2R,4R,5S,6S)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-2,4,6-trimethyloctan-3-ol

Guidance literature:: Multi-step reaction with 6 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 / -30 °C / Inert atmosphere

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere

6.1: 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

With triisopropoxytitanium(IV) chloride; Ir(cycloocta-1,5-diene)(C₁₀H₁₅C₃H₃NOC₂H₄N₂C₃H₂(C₆H₃(iPr)2) tetrakis(3,5-bis(trifluoromethyl)phenyl)borate; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; cyclopentylmagnesium chloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene;
DOI:10.1016/j.tet.2009.04.073