(2S,3S,4R,6S,7S,8S,9S)-2-((2S,4S,5R,6S)-6-ethyl-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-3-hydroxy-9-((4-methoxybenzyl)oxy)-4,6,8,10-tetramethyl-7-((triethylsilyl)oxy)undecan-5-one

Base Information

Chemical Name:(2S,3S,4R,6S,7S,8S,9S)-2-((2S,4S,5R,6S)-6-ethyl-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-3-hydroxy-9-((4-methoxybenzyl)oxy)-4,6,8,10-tetramethyl-7-((triethylsilyl)oxy)undecan-5-one
CAS No.:1380244-52-9
Molecular Formula:C₄₃H₇₀O₈Si
Molecular Weight:743.109
Hs Code.:

(2S,3S,4R,6S,7S,8S,9S)-2-((2S,4S,5R,6S)-6-ethyl-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-3-hydroxy-9-((4-methoxybenzyl)oxy)-4,6,8,10-tetramethyl-7-((triethylsilyl)oxy)undecan-5-one

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Chemical Property of (2S,3S,4R,6S,7S,8S,9S)-2-((2S,4S,5R,6S)-6-ethyl-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-3-hydroxy-9-((4-methoxybenzyl)oxy)-4,6,8,10-tetramethyl-7-((triethylsilyl)oxy)undecan-5-one

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Technology Process of (2S,3S,4R,6S,7S,8S,9S)-2-((2S,4S,5R,6S)-6-ethyl-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-3-hydroxy-9-((4-methoxybenzyl)oxy)-4,6,8,10-tetramethyl-7-((triethylsilyl)oxy)undecan-5-one

There total 10 articles about (2S,3S,4R,6S,7S,8S,9S)-2-((2S,4S,5R,6S)-6-ethyl-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-3-hydroxy-9-((4-methoxybenzyl)oxy)-4,6,8,10-tetramethyl-7-((triethylsilyl)oxy)undecan-5-one 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:

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 1380244-52-9
(2S,3S,4R,6S,7S,8S,9S)-2-((2S,4S,5R,6S)-6-ethyl-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-3-hydroxy-9-((4-methoxybenzyl)oxy)-4,6,8,10-tetramethyl-7-((triethylsilyl)oxy)undecan-5-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: toluene-4-sulfonic acid / 1 h / 40 °C / 1.2 Torr / Inert atmosphere

2.1: lithium borohydride / tetrahydrofuran; methanol / 3 h / 0 - 20 °C / Inert atmosphere

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

4.1: tin(II) trifluoromethanesulfonate; triethylamine / dichloromethane / 2 h / -78 °C / Inert atmosphere

4.2: 2 h / Inert atmosphere

With lithium borohydride; tin(II) trifluoromethanesulfonate; oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; 3.1: Swern oxidation / 3.2: Swern oxidation;
DOI:10.1002/anie.201109080

Reference yield:

: (2S,3S)-3-(4-methoxybenzyloxy)-2,4-dimethylpentanal

: 1380244-52-9
(2S,3S,4R,6S,7S,8S,9S)-2-((2S,4S,5R,6S)-6-ethyl-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-3-hydroxy-9-((4-methoxybenzyl)oxy)-4,6,8,10-tetramethyl-7-((triethylsilyl)oxy)undecan-5-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: dicyclohexylboron chloride; triethylamine / diethyl ether / 2.25 h / -78 - 0 °C / Inert atmosphere

1.2: 17 h / -17 °C / Inert atmosphere

2.1: 2,6-dimethylpyridine / dichloromethane / 0.83 h / -78 - 0 °C / Inert atmosphere

3.1: samarium diiodide / tetrahydrofuran; methanol / 1.25 h / 0 °C / Inert atmosphere

4.1: tin(II) trifluoromethanesulfonate; triethylamine / dichloromethane / 2 h / -78 °C / Inert atmosphere

4.2: 2 h / Inert atmosphere

With 2,6-dimethylpyridine; tin(II) trifluoromethanesulfonate; samarium diiodide; dicyclohexylboron chloride; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;
DOI:10.1002/anie.201109080

Reference yield:

: 1380244-50-7
(2R,4S,5S,6S,7S)-7-((4-methoxybenzyl)oxy)-4,6,8-trimethyl-3-oxo-5-((triethylsilyl)oxy)nonan-2-yl benzoate

: 1380244-52-9
(2S,3S,4R,6S,7S,8S,9S)-2-((2S,4S,5R,6S)-6-ethyl-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-3-hydroxy-9-((4-methoxybenzyl)oxy)-4,6,8,10-tetramethyl-7-((triethylsilyl)oxy)undecan-5-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: samarium diiodide / tetrahydrofuran; methanol / 1.25 h / 0 °C / Inert atmosphere

2.1: tin(II) trifluoromethanesulfonate; triethylamine / dichloromethane / 2 h / -78 °C / Inert atmosphere

2.2: 2 h / Inert atmosphere

With tin(II) trifluoromethanesulfonate; samarium diiodide; triethylamine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1002/anie.201109080