(2R,3R,4S)-(3S,4S,5S,6S)-3-((4-methoxybenzyl)oxy)-2,4,6-trimethyl-7-oxononan-5-yl 3-hydroxy-2,4-dimethyl-5-oxoheptanoate

Base Information

Chemical Name:(2R,3R,4S)-(3S,4S,5S,6S)-3-((4-methoxybenzyl)oxy)-2,4,6-trimethyl-7-oxononan-5-yl 3-hydroxy-2,4-dimethyl-5-oxoheptanoate
CAS No.:1380244-56-3
Molecular Formula:C₂₉H₄₆O₇
Molecular Weight:506.68
Hs Code.:

Synonyms:(2R,3R,4S)-(3S,4S,5S,6S)-3-((4-methoxybenzyl)oxy)-2,4,6-trimethyl-7-oxononan-5-yl 3-hydroxy-2,4-dimethyl-5-oxoheptanoate

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

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

There total 36 articles about (2R,3R,4S)-(3S,4S,5S,6S)-3-((4-methoxybenzyl)oxy)-2,4,6-trimethyl-7-oxononan-5-yl 3-hydroxy-2,4-dimethyl-5-oxoheptanoate 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: 64.0%

: 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

: 1380244-56-3
(2R,3R,4S)-(3S,4S,5S,6S)-3-((4-methoxybenzyl)oxy)-2,4,6-trimethyl-7-oxononan-5-yl 3-hydroxy-2,4-dimethyl-5-oxoheptanoate

Guidance literature:: With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;
DOI:10.1002/anie.201109080

Reference yield: 63.0%

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

: 1380244-56-3
(2R,3R,4S)-(3S,4S,5S,6S)-3-((4-methoxybenzyl)oxy)-2,4,6-trimethyl-7-oxononan-5-yl 3-hydroxy-2,4-dimethyl-5-oxoheptanoate

Guidance literature:: With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1002/ejoc.201701748

Reference yield:

: ethyl (4R,5S,E)-5-[(4-methoxybenzyl)oxy]-4,6-dimethylhept-2-enoate

: 1380244-56-3
(2R,3R,4S)-(3S,4S,5S,6S)-3-((4-methoxybenzyl)oxy)-2,4,6-trimethyl-7-oxononan-5-yl 3-hydroxy-2,4-dimethyl-5-oxoheptanoate

Guidance literature:: Multi-step reaction with 11 steps

1.1: diisobutylaluminium hydride / toluene; dichloromethane / 1 h / 0 - 20 °C

2.1: titanium(IV) isopropylate; L-(+)-diisopropyl tartrate; tert.-butylhydroperoxide / dichloromethane / 10.5 h / -20 °C / Molecular sieve

3.1: copper(l) iodide / tetrahydrofuran / 0.5 h / -20 °C

3.2: 15 h / -25 - 0 °C

4.1: triethylamine / dichloromethane / 4 h / 0 °C

5.1: triethylamine; dmap; 2,4,6-trichlorobenzoyl chloride / toluene / 6 h / 0 - 20 °C

6.1: diisobutylaluminium hydride / toluene; dichloromethane / 0.08 h / -78 °C

7.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane; dimethyl sulfoxide / 2 h / 20 °C

8.1: tetrahydrofuran / 1 h / 0 - 20 °C

9.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane; dimethyl sulfoxide / 2 h / 20 °C

10.1: pyridine hydrogenfluoride / tetrahydrofuran / 0 - 20 °C

11.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 1 h / 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; copper(l) iodide; L-(+)-diisopropyl tartrate; 2,4,6-trichlorobenzoyl chloride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; toluene; 2.1: |Sharpless Asymmetric Epoxidation / 5.1: |Yamaguchi Lactonization;
DOI:10.1002/ejoc.201701748