(R)-2-((2S,4S,5R,6S)-6-((S)-but-3-en-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)propanoic acid

Base Information

Chemical Name:(R)-2-((2S,4S,5R,6S)-6-((S)-but-3-en-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)propanoic acid
CAS No.:1426447-42-8
Molecular Formula:C₁₉H₂₆O₅
Molecular Weight:334.412
Hs Code.:

Synonyms:(R)-2-((2S,4S,5R,6S)-6-((S)-but-3-en-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)propanoic acid

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Chemical Property of (R)-2-((2S,4S,5R,6S)-6-((S)-but-3-en-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)propanoic acid

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Technology Process of (R)-2-((2S,4S,5R,6S)-6-((S)-but-3-en-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)propanoic acid

There total 7 articles about (R)-2-((2S,4S,5R,6S)-6-((S)-but-3-en-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)propanoic 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: 80.0%

: 1426447-41-7
(2R,3S,4S,5S,6S)-3-hydroxy-5-((4-methoxybenzyl)oxy)-2,4,6-trimethyloct-7-enoic acid

: 1426447-42-8
(R)-2-((2S,4S,5R,6S)-6-((S)-but-3-en-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)propanoic acid

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere; Molecular sieve;
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

: 1426447-42-8
(R)-2-((2S,4S,5R,6S)-6-((S)-but-3-en-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)propanoic acid

Guidance literature:: Multi-step reaction with 5 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

3.1: (2-methylpropyl)lithium / tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide / 2 h / -78 - -20 °C / Inert atmosphere

3.2: 2 h / Inert atmosphere

4.1: lithium hydroxide monohydrate; water / 1,4-dioxane / 25 °C / Inert atmosphere

5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 0 °C / Inert atmosphere; Molecular sieve

With osmium(VIII) oxide; lithium hydroxide monohydrate; water; (2-methylpropyl)lithium; sodium hydrogencarbonate; ammonium chloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc; In tetrahydrofuran; 1,4-dioxane; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/ja4008722

Reference yield:

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

: 1426447-42-8
(R)-2-((2S,4S,5R,6S)-6-((S)-but-3-en-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)propanoic acid

Guidance literature:: Multi-step reaction with 3 steps

1.1: (2-methylpropyl)lithium / tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide / 2 h / -78 - -20 °C / Inert atmosphere

1.2: 2 h / Inert atmosphere

2.1: lithium hydroxide monohydrate; water / 1,4-dioxane / 25 °C / Inert atmosphere

3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 0 °C / Inert atmosphere; Molecular sieve

With lithium hydroxide monohydrate; water; (2-methylpropyl)lithium; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; 1,4-dioxane; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;
DOI:10.1021/ja4008722