(2S)-2-[(1S,2R)-1-hydroxy-2-p-methoxybenzyloxy-but-3-enyl]-3,7-dimethyloct-3,6-dienoic acid methoxy-N-methyl-amide

Base Information

Chemical Name:(2S)-2-[(1S,2R)-1-hydroxy-2-p-methoxybenzyloxy-but-3-enyl]-3,7-dimethyloct-3,6-dienoic acid methoxy-N-methyl-amide
CAS No.:364337-22-4
Molecular Formula:C₂₄H₃₅NO₅
Molecular Weight:417.546
Hs Code.:

Synonyms:(2S)-2-[(1S,2R)-1-hydroxy-2-p-methoxybenzyloxy-but-3-enyl]-3,7-dimethyloct-3,6-dienoic acid methoxy-N-methyl-amide

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Chemical Property of (2S)-2-[(1S,2R)-1-hydroxy-2-p-methoxybenzyloxy-but-3-enyl]-3,7-dimethyloct-3,6-dienoic acid methoxy-N-methyl-amide

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Technology Process of (2S)-2-[(1S,2R)-1-hydroxy-2-p-methoxybenzyloxy-but-3-enyl]-3,7-dimethyloct-3,6-dienoic acid methoxy-N-methyl-amide

There total 9 articles about (2S)-2-[(1S,2R)-1-hydroxy-2-p-methoxybenzyloxy-but-3-enyl]-3,7-dimethyloct-3,6-dienoic acid methoxy-N-methyl-amide 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: 71.0%

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

: 364337-21-3
(4R)-4-benzyl-3-{(2S)-2-[(1S,2R)-1-hydroxy-2-p-methoxybenzyloxy-but-3-enyl]-3,7-dimethyloct-3,6-dienoyl}-oxazolidin-2-one

: 364337-22-4
(2S)-2-[(1S,2R)-1-hydroxy-2-p-methoxybenzyloxy-but-3-enyl]-3,7-dimethyloct-3,6-dienoic acid methoxy-N-methyl-amide

Guidance literature:: N,O-dimethylhydroxylamine*hydrochloride; With trimethylaluminum; In tetrahydrofuran; toluene; at 20 ℃; for 0.75h;

(4R)-4-benzyl-3-{(2S)-2-[(1S,2R)-1-hydroxy-2-p-methoxybenzyloxy-but-3-enyl]-3,7-dimethyloct-3,6-dienoyl}-oxazolidin-2-one; In tetrahydrofuran; toluene; at 0 ℃; Further stages.;
DOI:10.1021/ol016343z

Reference yield:

: 16750-94-0
2,6-dimethyl-2,5-octadien-8-ol

: 364337-22-4
(2S)-2-[(1S,2R)-1-hydroxy-2-p-methoxybenzyloxy-but-3-enyl]-3,7-dimethyloct-3,6-dienoic acid methoxy-N-methyl-amide

Guidance literature:: Multi-step reaction with 6 steps

1.1: 35 percent / CrO₃; sulfuric acid / H₂O; acetone / 0.25 h / 0 °C

2.1: triethylamine / tetrahydrofuran / 0.5 h / -78 - 0 °C

3.1: 188 mg / tetrahydrofuran; hexane / 0.33 h / -78 °C

4.1: LDA / tetrahydrofuran; hexane / 0.75 h / -78 °C

4.2: tetrahydrofuran; hexane / 0.75 h / -78 °C

5.1: 4.61 g / tetrabutylammonium periodate / CHCl₃ / 2 h / 60 °C

6.1: trimethylaluminium / toluene; tetrahydrofuran / 0.75 h / 20 °C

6.2: 71 percent / toluene; tetrahydrofuran / 0 °C

With chromium(VI) oxide; sulfuric acid; trimethylaluminum; tetrabutylammonium periodite; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; chloroform; water; acetone; toluene;
DOI:10.1021/ol016343z

Reference yield:

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

: 364337-22-4
(2S)-2-[(1S,2R)-1-hydroxy-2-p-methoxybenzyloxy-but-3-enyl]-3,7-dimethyloct-3,6-dienoic acid methoxy-N-methyl-amide

Guidance literature:: Multi-step reaction with 5 steps

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

2.1: 94 percent / DIBAH / toluene / 0.33 h / -78 °C

3.1: LDA / tetrahydrofuran; hexane / 0.75 h / -78 °C

3.2: tetrahydrofuran; hexane / 0.75 h / -78 °C

4.1: 4.61 g / tetrabutylammonium periodate / CHCl₃ / 2 h / 60 °C

5.1: trimethylaluminium / toluene; tetrahydrofuran / 0.75 h / 20 °C

5.2: 71 percent / toluene; tetrahydrofuran / 0 °C

With camphor-10-sulfonic acid; trimethylaluminum; diisobutylaluminium hydride; tetrabutylammonium periodite; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; chloroform; toluene;
DOI:10.1021/ol016343z