(2R,3R,4R,5S)-(3S,4S,5S,6S)-3-((4-methoxybenzyl)oxy)-2,4,6-trimethyl-7-oxononan-5-yl 3,5-dihydroxy-2,4-dimethylheptanoate

Base Information

Chemical Name:(2R,3R,4R,5S)-(3S,4S,5S,6S)-3-((4-methoxybenzyl)oxy)-2,4,6-trimethyl-7-oxononan-5-yl 3,5-dihydroxy-2,4-dimethylheptanoate
CAS No.:1380244-55-2
Molecular Formula:C₂₉H₄₈O₇
Molecular Weight:508.696
Hs Code.:

Synonyms:(2R,3R,4R,5S)-(3S,4S,5S,6S)-3-((4-methoxybenzyl)oxy)-2,4,6-trimethyl-7-oxononan-5-yl 3,5-dihydroxy-2,4-dimethylheptanoate

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Chemical Property of (2R,3R,4R,5S)-(3S,4S,5S,6S)-3-((4-methoxybenzyl)oxy)-2,4,6-trimethyl-7-oxononan-5-yl 3,5-dihydroxy-2,4-dimethylheptanoate

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Technology Process of (2R,3R,4R,5S)-(3S,4S,5S,6S)-3-((4-methoxybenzyl)oxy)-2,4,6-trimethyl-7-oxononan-5-yl 3,5-dihydroxy-2,4-dimethylheptanoate

There total 13 articles about (2R,3R,4R,5S)-(3S,4S,5S,6S)-3-((4-methoxybenzyl)oxy)-2,4,6-trimethyl-7-oxononan-5-yl 3,5-dihydroxy-2,4-dimethylheptanoate 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: 92.0%

: 1380244-54-1
(R)-(3S,4S,5S,6S)-3-((4-methoxybenzyl)oxy)-2,4,6-trimethyl-7-oxononan-5-yl 2-((2S,4R,5R,6S)-6-ethyl-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)propanoate

: 1380244-55-2
(2R,3R,4R,5S)-(3S,4S,5S,6S)-3-((4-methoxybenzyl)oxy)-2,4,6-trimethyl-7-oxononan-5-yl 3,5-dihydroxy-2,4-dimethylheptanoate

Guidance literature:: With camphor-10-sulfonic acid; In methanol; at 20 ℃; for 0.75h; Inert atmosphere;
DOI:10.1002/anie.201109080

Reference yield:

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

: 1380244-55-2
(2R,3R,4R,5S)-(3S,4S,5S,6S)-3-((4-methoxybenzyl)oxy)-2,4,6-trimethyl-7-oxononan-5-yl 3,5-dihydroxy-2,4-dimethylheptanoate

Guidance literature:: Multi-step reaction with 8 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

6.1: pyridine; pyridine hydrogenfluoride / tetrahydrofuran / 3.5 h / 20 °C / Inert atmosphere

7.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 19 h / 20 °C / Inert atmosphere

8.1: camphor-10-sulfonic acid / methanol / 0.75 h / 20 °C / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; tin(II) trifluoromethanesulfonate; samarium diiodide; camphor-10-sulfonic acid; dicyclohexylboron chloride; sodium hydrogencarbonate; Dess-Martin periodane; pyridine hydrogenfluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; benzene; 7.1: retro-Claisen rearrangement;
DOI:10.1002/anie.201109080

Reference yield:

: 1380244-51-8
(4S,5S,6S,7S)-7-((4-methoxybenzyl)oxy)-4,6,8-trimethyl-5-((triethylsilyl)oxy)nonan-3-one

: 1380244-55-2
(2R,3R,4R,5S)-(3S,4S,5S,6S)-3-((4-methoxybenzyl)oxy)-2,4,6-trimethyl-7-oxononan-5-yl 3,5-dihydroxy-2,4-dimethylheptanoate

Guidance literature:: Multi-step reaction with 5 steps

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

1.2: 2 h / Inert atmosphere

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

3.1: pyridine; pyridine hydrogenfluoride / tetrahydrofuran / 3.5 h / 20 °C / Inert atmosphere

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 19 h / 20 °C / Inert atmosphere

5.1: camphor-10-sulfonic acid / methanol / 0.75 h / 20 °C / Inert atmosphere

With pyridine; tin(II) trifluoromethanesulfonate; camphor-10-sulfonic acid; sodium hydrogencarbonate; Dess-Martin periodane; pyridine hydrogenfluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; dichloromethane; benzene; 4.1: retro-Claisen rearrangement;
DOI:10.1002/anie.201109080