(2R,3R,4S,5S,6S)-3-hydroxy-5-((4-methoxybenzyl)oxy)-2,4,6-trimethyloct-7-enoic acid

Base Information

Chemical Name:(2R,3R,4S,5S,6S)-3-hydroxy-5-((4-methoxybenzyl)oxy)-2,4,6-trimethyloct-7-enoic acid
CAS No.:1426447-33-7
Molecular Formula:C₁₉H₂₈O₅
Molecular Weight:336.428
Hs Code.:

Synonyms:(2R,3R,4S,5S,6S)-3-hydroxy-5-((4-methoxybenzyl)oxy)-2,4,6-trimethyloct-7-enoic acid

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Chemical Property of (2R,3R,4S,5S,6S)-3-hydroxy-5-((4-methoxybenzyl)oxy)-2,4,6-trimethyloct-7-enoic acid

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Technology Process of (2R,3R,4S,5S,6S)-3-hydroxy-5-((4-methoxybenzyl)oxy)-2,4,6-trimethyloct-7-enoic acid

There total 4 articles about (2R,3R,4S,5S,6S)-3-hydroxy-5-((4-methoxybenzyl)oxy)-2,4,6-trimethyloct-7-enoic acid 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%

: 1426447-40-6
(R)-2-((2R,3R,4R,5R,6S)-6-(iodomethyl)-4-((4-methoxybenzyl)oxy)-3,5-dimethyltetrahydro-2H-pyran-2-yl)propanoic acid

: 1426447-33-7
(2R,3R,4S,5S,6S)-3-hydroxy-5-((4-methoxybenzyl)oxy)-2,4,6-trimethyloct-7-enoic acid

Guidance literature:: With ammonium chloride; zinc; In ethanol; for 1h; Reflux; Inert atmosphere;
DOI:10.1021/ja4008722

Reference yield:

: 1426447-32-6
(2S,3R,4R,5R,6S)-2-((S)-but-3-en-2-yl)-6-(iodomethyl)-4-((4-methoxybenzyl)oxy)-3,5-dimethyltetrahydro-2H-pyran

: 1426447-33-7
(2R,3R,4S,5S,6S)-3-hydroxy-5-((4-methoxybenzyl)oxy)-2,4,6-trimethyloct-7-enoic acid

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium hydrogencarbonate; osmium(VIII) oxide / water; N,N-dimethyl-formamide; tert-butyl alcohol / 0.08 h / 25 °C / Inert atmosphere

1.2: 6 h / 25 °C

2.1: zinc; ammonium chloride / ethanol / 1 h / Reflux; Inert atmosphere

With osmium(VIII) oxide; sodium hydrogencarbonate; ammonium chloride; zinc; In ethanol; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/ja4008722

Reference yield:

: 1426447-39-3
(2S,3R,4R,5R,6S)-2-((S)-but-3-en-2-yl)-6-(iodomethyl)-3,5-dimethyltetrahydro-2H-pyran-4-ol

: 1426447-33-7
(2R,3R,4S,5S,6S)-3-hydroxy-5-((4-methoxybenzyl)oxy)-2,4,6-trimethyloct-7-enoic acid

Guidance literature:: Multi-step reaction with 3 steps

1.1: camphor-10-sulfonic acid / diethyl ether / 30 °C / Inert atmosphere

2.1: sodium hydrogencarbonate; osmium(VIII) oxide / water; N,N-dimethyl-formamide; tert-butyl alcohol / 0.08 h / 25 °C / Inert atmosphere

2.2: 6 h / 25 °C

3.1: zinc; ammonium chloride / ethanol / 1 h / Reflux; Inert atmosphere

With osmium(VIII) oxide; camphor-10-sulfonic acid; sodium hydrogencarbonate; ammonium chloride; zinc; In diethyl ether; ethanol; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/ja4008722