(2S,5R)-6-(4-Methoxy-benzyloxy)-5-methyl-4-methylene-1-((S)-2-methyl-oxiranyl)-hexan-2-ol

Base Information

Chemical Name:(2S,5R)-6-(4-Methoxy-benzyloxy)-5-methyl-4-methylene-1-((S)-2-methyl-oxiranyl)-hexan-2-ol
CAS No.:410077-46-2
Molecular Formula:C₁₉H₂₈O₄
Molecular Weight:320.429
Hs Code.:

Synonyms:(2S,5R)-6-(4-Methoxy-benzyloxy)-5-methyl-4-methylene-1-((S)-2-methyl-oxiranyl)-hexan-2-ol

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Chemical Property of (2S,5R)-6-(4-Methoxy-benzyloxy)-5-methyl-4-methylene-1-((S)-2-methyl-oxiranyl)-hexan-2-ol

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Technology Process of (2S,5R)-6-(4-Methoxy-benzyloxy)-5-methyl-4-methylene-1-((S)-2-methyl-oxiranyl)-hexan-2-ol

There total 11 articles about (2S,5R)-6-(4-Methoxy-benzyloxy)-5-methyl-4-methylene-1-((S)-2-methyl-oxiranyl)-hexan-2-ol 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: 74.0%

: 410077-70-2
(2S,4S,7R)-8-(4-Methoxy-benzyloxy)-2,7-dimethyl-6-methylene-octane-1,2,4-triol

: 410077-46-2
(2S,5R)-6-(4-Methoxy-benzyloxy)-5-methyl-4-methylene-1-((S)-2-methyl-oxiranyl)-hexan-2-ol

Guidance literature:: (2S,4S,7R)-8-(4-Methoxy-benzyloxy)-2,7-dimethyl-6-methylene-octane-1,2,4-triol; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 1h; Inert atmosphere;

With 1-[(2,4,6-triisopropylphenyl)sulfonyl]-1H-imidazole; In tetrahydrofuran; at 0 ℃; for 1.5h; Inert atmosphere;
DOI:10.1016/j.tet.2009.04.003

Reference yield:

: 410077-43-9
C₂₈H₄₂N₂O₄S

: 410077-46-2
(2S,5R)-6-(4-Methoxy-benzyloxy)-5-methyl-4-methylene-1-((S)-2-methyl-oxiranyl)-hexan-2-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: t-BuLi / tetrahydrofuran; pentane / 1 h / -78 - 0 °C

1.2: 88 percent / n-BuLi / tetrahydrofuran; pentane; hexane / 3 h / -45 - 0 °C

2.1: 98 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C

3.1: NaH / tetrahydrofuran / 1 h / 0 °C

3.2: 73 percent / 2,4,6-triisopropylbenzenesulfonyl imidazole / tetrahydrofuran / 1.5 h / 0 °C

With tetrabutyl ammonium fluoride; tert.-butyl lithium; sodium hydride; In tetrahydrofuran; pentane;
DOI:10.1021/ol017273z

Reference yield:

: 56599-24-7
p-methoxybenzyl trichloroacetate

: 410077-46-2
(2S,5R)-6-(4-Methoxy-benzyloxy)-5-methyl-4-methylene-1-((S)-2-methyl-oxiranyl)-hexan-2-ol

Guidance literature:: Multi-step reaction with 7 steps

1.1: p-TsOH / CH₂Cl₂

2.1: 90 percent / i-PrMgCl / tetrahydrofuran / 0.33 h / -20 °C

3.1: 95 percent / tetrahydrofuran / 0.33 h / 0 °C

4.1: 90 percent / tetrahydrofuran / 12 h / 0 - 20 °C

5.1: t-BuLi / tetrahydrofuran; pentane / 1 h / -78 - 0 °C

5.2: 88 percent / n-BuLi / tetrahydrofuran; pentane; hexane / 3 h / -45 - 0 °C

6.1: 98 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C

7.1: NaH / tetrahydrofuran / 1 h / 0 °C

7.2: 73 percent / 2,4,6-triisopropylbenzenesulfonyl imidazole / tetrahydrofuran / 1.5 h / 0 °C

With tetrabutyl ammonium fluoride; tert.-butyl lithium; isopropylmagnesium chloride; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; pentane;
DOI:10.1021/ol017273z