(2S)-N-methoxy-2-[(4R,6R)-6-((1E)-1-{[(4-methoxybenzyl)oxy]methyl}but-1-enyl)-2,2-dimethyl-1,3-dioxan-4-yl]-N-methylpentanamide

Base Information

Chemical Name:(2S)-N-methoxy-2-[(4R,6R)-6-((1E)-1-{[(4-methoxybenzyl)oxy]methyl}but-1-enyl)-2,2-dimethyl-1,3-dioxan-4-yl]-N-methylpentanamide
CAS No.:912654-43-4
Molecular Formula:C₂₆H₄₁NO₆
Molecular Weight:463.615
Hs Code.:

Synonyms:(2S)-N-methoxy-2-[(4R,6R)-6-((1E)-1-{[(4-methoxybenzyl)oxy]methyl}but-1-enyl)-2,2-dimethyl-1,3-dioxan-4-yl]-N-methylpentanamide

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Chemical Property of (2S)-N-methoxy-2-[(4R,6R)-6-((1E)-1-{[(4-methoxybenzyl)oxy]methyl}but-1-enyl)-2,2-dimethyl-1,3-dioxan-4-yl]-N-methylpentanamide

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Technology Process of (2S)-N-methoxy-2-[(4R,6R)-6-((1E)-1-{[(4-methoxybenzyl)oxy]methyl}but-1-enyl)-2,2-dimethyl-1,3-dioxan-4-yl]-N-methylpentanamide

There total 13 articles about (2S)-N-methoxy-2-[(4R,6R)-6-((1E)-1-{[(4-methoxybenzyl)oxy]methyl}but-1-enyl)-2,2-dimethyl-1,3-dioxan-4-yl]-N-methylpentanamide 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: 92.0%

: 912654-42-3
(2S,3R,5R,6E)-3,5-dihydroxy-N-methoxy-6-{[(4-methoxybenzyl)oxy]methyl}-N-methyl-2-propylnon-6-enamide

: 77-76-9
2,2-dimethoxy-propane

: 912654-43-4
(2S)-N-methoxy-2-[(4R,6R)-6-((1E)-1-{[(4-methoxybenzyl)oxy]methyl}but-1-enyl)-2,2-dimethyl-1,3-dioxan-4-yl]-N-methylpentanamide

Guidance literature:: With camphor-10-sulfonic acid; In tetrahydrofuran; at 20 ℃; for 4h;
DOI:10.1021/jo061104g

Reference yield:

: 912654-35-4
(2E)-2-{[(4-methoxybenzyl)oxy]methyl}pent-2-enal

: 912654-43-4
(2S)-N-methoxy-2-[(4R,6R)-6-((1E)-1-{[(4-methoxybenzyl)oxy]methyl}but-1-enyl)-2,2-dimethyl-1,3-dioxan-4-yl]-N-methylpentanamide

Guidance literature:: Multi-step reaction with 8 steps

1.1: TiCl₄ / CH₂Cl₂ / 0.08 h / 0 °C

1.2: iPr₂NEt / CH₂Cl₂ / 2 h / -78 °C

1.3: 70 percent / CH₂Cl₂ / 0.5 h / -78 °C

2.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 23 °C

3.1: 84 percent / NaBH₄ / tetrahydrofuran; H₂O / 0 °C

4.1: 91 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 3.5 h / -78 - 20 °C

5.1: Bu₂BOTf; triethylamine / CH₂Cl₂ / 0.25 h / 0 °C

5.2: CH₂Cl₂ / 1.5 h / -78 - 20 °C

6.1: 66 percent / AlMe₃ / tetrahydrofuran; toluene / 16 h / 0 - 20 °C

7.1: 88 percent / TBAF / tetrahydrofuran / 12 h / 0 °C

8.1: 92 percent / CSA / tetrahydrofuran / 4 h / 20 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; trimethylaluminum; titanium tetrachloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; water; toluene; 5.2: Evans aldol reaction;
DOI:10.1021/jo061104g

Reference yield:

: 912654-34-3
(2Z)-2-{[(4-methoxybenzyl)oxy]methyl}pent-2-en-1-ol

: 912654-43-4
(2S)-N-methoxy-2-[(4R,6R)-6-((1E)-1-{[(4-methoxybenzyl)oxy]methyl}but-1-enyl)-2,2-dimethyl-1,3-dioxan-4-yl]-N-methylpentanamide

Guidance literature:: Multi-step reaction with 9 steps

1.1: 91 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 3.5 h / -78 - 20 °C

2.1: TiCl₄ / CH₂Cl₂ / 0.08 h / 0 °C

2.2: iPr₂NEt / CH₂Cl₂ / 2 h / -78 °C

2.3: 70 percent / CH₂Cl₂ / 0.5 h / -78 °C

3.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 23 °C

4.1: 84 percent / NaBH₄ / tetrahydrofuran; H₂O / 0 °C

5.1: 91 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 3.5 h / -78 - 20 °C

6.1: Bu₂BOTf; triethylamine / CH₂Cl₂ / 0.25 h / 0 °C

6.2: CH₂Cl₂ / 1.5 h / -78 - 20 °C

7.1: 66 percent / AlMe₃ / tetrahydrofuran; toluene / 16 h / 0 - 20 °C

8.1: 88 percent / TBAF / tetrahydrofuran / 12 h / 0 °C

9.1: 92 percent / CSA / tetrahydrofuran / 4 h / 20 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; trimethylaluminum; titanium tetrachloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; water; toluene; 6.2: Evans aldol reaction;
DOI:10.1021/jo061104g