(2S)-2-[(1S,2R)-1-hydroxy-2-p-methoxybenzyloxybut-3-enyl]-3,7-dimethylocta-3-enoic acid methoxymethylamide

Base Information

Chemical Name:(2S)-2-[(1S,2R)-1-hydroxy-2-p-methoxybenzyloxybut-3-enyl]-3,7-dimethylocta-3-enoic acid methoxymethylamide
CAS No.:527754-90-1
Molecular Formula:C₂₄H₃₇NO₅
Molecular Weight:419.561
Hs Code.:

Synonyms:(2S)-2-[(1S,2R)-1-hydroxy-2-p-methoxybenzyloxybut-3-enyl]-3,7-dimethylocta-3-enoic acid methoxymethylamide

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Chemical Property of (2S)-2-[(1S,2R)-1-hydroxy-2-p-methoxybenzyloxybut-3-enyl]-3,7-dimethylocta-3-enoic acid methoxymethylamide

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Technology Process of (2S)-2-[(1S,2R)-1-hydroxy-2-p-methoxybenzyloxybut-3-enyl]-3,7-dimethylocta-3-enoic acid methoxymethylamide

There total 12 articles about (2S)-2-[(1S,2R)-1-hydroxy-2-p-methoxybenzyloxybut-3-enyl]-3,7-dimethylocta-3-enoic acid methoxymethylamide 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: 75.0%

: 6638-79-5
N,O-dimethylhydroxylamine*hydrochloride

: 527754-88-7
(4R)-4-benzyl-3-[(2S)-2-[(1S,2R)-1-hydroxy-2-p-methoxybenzyloxybut-3-enyl]-3,7-dimethylocta-3-enoyl]oxazolidin-2-one

: 527754-90-1
(2S)-2-[(1S,2R)-1-hydroxy-2-p-methoxybenzyloxybut-3-enyl]-3,7-dimethylocta-3-enoic acid methoxymethylamide

Guidance literature:: N,O-dimethylhydroxylamine*hydrochloride; With trimethylaluminum; In tetrahydrofuran; toluene; at 20 ℃; for 0.5h;

(4R)-4-benzyl-3-[(2S)-2-[(1S,2R)-1-hydroxy-2-p-methoxybenzyloxybut-3-enyl]-3,7-dimethylocta-3-enoyl]oxazolidin-2-one; In tetrahydrofuran; toluene; at 20 ℃; for 24h;
DOI:10.1021/jo035065+

Reference yield:

: 56134-54-4
(E)-3,7-dimethyloct-3-enol

: 527754-90-1
(2S)-2-[(1S,2R)-1-hydroxy-2-p-methoxybenzyloxybut-3-enyl]-3,7-dimethylocta-3-enoic acid methoxymethylamide

Guidance literature:: Multi-step reaction with 6 steps

1.1: 65 percent / CrO₃; H₂SO₄ / H₂O; acetone / 0.25 h / 0 °C

2.1: oxalyl chloride; DMF / CH₂Cl₂ / 4 h / 0 - 20 °C

3.1: 9.16 g / BuLi / tetrahydrofuran; hexane / -78 - 0 °C

4.1: lithium diisopropylamide / tetrahydrofuran; hexane / 0.5 h / -78 °C

4.2: 55 percent / tetrahydrofuran; hexane / 1 h / -78 °C

5.1: 5.83 g / tetrabutylammonium periodate / CHCl₃ / 2 h / 60 °C

6.1: trimethylaluminum / toluene; tetrahydrofuran / 0.5 h / 20 °C

6.2: 75 percent / toluene; tetrahydrofuran / 24 h / 20 °C

With chromium(VI) oxide; n-butyllithium; oxalyl dichloride; sulfuric acid; trimethylaluminum; tetrabutylammonium periodite; N,N-dimethyl-formamide; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; chloroform; water; acetone; toluene;
DOI:10.1021/jo035065+

Reference yield:

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 527754-90-1
(2S)-2-[(1S,2R)-1-hydroxy-2-p-methoxybenzyloxybut-3-enyl]-3,7-dimethylocta-3-enoic acid methoxymethylamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: 70 percent / camphorsulfonic acid / CH₂Cl₂ / 24 h / 20 °C

2.1: DIBAL-H / toluene / 0.33 h / -78 °C

3.1: lithium diisopropylamide / tetrahydrofuran; hexane / 0.5 h / -78 °C

3.2: 55 percent / tetrahydrofuran; hexane / 1 h / -78 °C

4.1: 5.83 g / tetrabutylammonium periodate / CHCl₃ / 2 h / 60 °C

5.1: trimethylaluminum / toluene; tetrahydrofuran / 0.5 h / 20 °C

5.2: 75 percent / toluene; tetrahydrofuran / 24 h / 20 °C

With camphor-10-sulfonic acid; trimethylaluminum; diisobutylaluminium hydride; tetrabutylammonium periodite; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; chloroform; toluene;
DOI:10.1021/jo035065+