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

Base Information

Chemical Name:(2S)-2-[(1S,2R)-1-methoxy-2-p-methoxybenzyloxybut-3-enyl]-3,7-dimethylocta-3-enoic acid methoxymethylamide
CAS No.:527754-92-3
Molecular Formula:C₂₅H₃₉NO₅
Molecular Weight:433.588
Hs Code.:

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

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

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

There total 13 articles about (2S)-2-[(1S,2R)-1-methoxy-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: 93.0%

: 74-88-4
methyl iodide

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

: 527754-92-3
(2S)-2-[(1S,2R)-1-methoxy-2-p-methoxybenzyloxybut-3-enyl]-3,7-dimethylocta-3-enoic acid methoxymethylamide

Guidance literature:: With silver(l) oxide; In diethyl ether; at 45 ℃; for 8h;
DOI:10.1021/jo035065+

Reference yield:

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

: 527754-92-3
(2S)-2-[(1S,2R)-1-methoxy-2-p-methoxybenzyloxybut-3-enyl]-3,7-dimethylocta-3-enoic acid methoxymethylamide

Guidance literature:: Multi-step reaction with 7 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

7.1: 93 percent / Ag₂O / diethyl ether / 8 h / 45 °C

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

Reference yield:

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

: 527754-92-3
(2S)-2-[(1S,2R)-1-methoxy-2-p-methoxybenzyloxybut-3-enyl]-3,7-dimethylocta-3-enoic acid methoxymethylamide

Guidance literature:: Multi-step reaction with 6 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

6.1: 93 percent / Ag₂O / diethyl ether / 8 h / 45 °C

With camphor-10-sulfonic acid; trimethylaluminum; diisobutylaluminium hydride; tetrabutylammonium periodite; silver(l) oxide; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; chloroform; toluene;
DOI:10.1021/jo035065+