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

Base Information

Chemical Name:(2R,4R,6S,7S,8S,9S)-2-((2S,4R,5R,6S)-6-ethyl-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-9-((4-methoxybenzyl)oxy)-4,6,8,10-tetramethyl-7-((triethylsilyl)oxy)undecane-3,5-dione
CAS No.:1380244-53-0
Molecular Formula:C₄₃H₆₈O₈Si
Molecular Weight:741.094
Hs Code.:

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

Synonyms:(2R,4R,6S,7S,8S,9S)-2-((2S,4R,5R,6S)-6-ethyl-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-9-((4-methoxybenzyl)oxy)-4,6,8,10-tetramethyl-7-((triethylsilyl)oxy)undecane-3,5-dione

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

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

There total 14 articles about (2R,4R,6S,7S,8S,9S)-2-((2S,4R,5R,6S)-6-ethyl-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-9-((4-methoxybenzyl)oxy)-4,6,8,10-tetramethyl-7-((triethylsilyl)oxy)undecane-3,5-dione 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: 88.0%

: (2S,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

: 1380244-53-0
(2R,4R,6S,7S,8S,9S)-2-((2S,4R,5R,6S)-6-ethyl-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-9-((4-methoxybenzyl)oxy)-4,6,8,10-tetramethyl-7-((triethylsilyl)oxy)undecane-3,5-dione

Guidance literature:: With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere;
DOI:10.1002/anie.201109080

Reference yield:

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 1380244-53-0
(2R,4R,6S,7S,8S,9S)-2-((2S,4R,5R,6S)-6-ethyl-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-9-((4-methoxybenzyl)oxy)-4,6,8,10-tetramethyl-7-((triethylsilyl)oxy)undecane-3,5-dione

Guidance literature:: Multi-step reaction with 5 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

5.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 2 h / 20 °C / Inert atmosphere

With lithium borohydride; tin(II) trifluoromethanesulfonate; oxalyl dichloride; sodium hydrogencarbonate; Dess-Martin periodane; 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

: 1380244-53-0
(2R,4R,6S,7S,8S,9S)-2-((2S,4R,5R,6S)-6-ethyl-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-9-((4-methoxybenzyl)oxy)-4,6,8,10-tetramethyl-7-((triethylsilyl)oxy)undecane-3,5-dione

Guidance literature:: Multi-step reaction with 5 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

5.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 2 h / 20 °C / Inert atmosphere

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