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

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Chemical Name:(2S)-2-[(4R,6R)-6-((1E)-1-{[(4-methoxybenzyl)oxy]methyl}but-1-enyl)-2,2-dimethyl-1,3-dioxan-4-yl]pentanal
CAS No.:912654-44-5
Molecular Formula:C₂₄H₃₆O₅
Molecular Weight:404.547
Hs Code.:

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

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

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

There total 14 articles about (2S)-2-[(4R,6R)-6-((1E)-1-{[(4-methoxybenzyl)oxy]methyl}but-1-enyl)-2,2-dimethyl-1,3-dioxan-4-yl]pentanal 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: 76.0%

: 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

: 912654-44-5
(2S)-2-[(4R,6R)-6-((1E)-1-{[(4-methoxybenzyl)oxy]methyl}but-1-enyl)-2,2-dimethyl-1,3-dioxan-4-yl]pentanal

Guidance literature:: With diisobutylaluminium hydride; In tetrahydrofuran; at -78 ℃; for 3h;
DOI:10.1021/jo061104g

Reference yield:

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

: 912654-44-5
(2S)-2-[(4R,6R)-6-((1E)-1-{[(4-methoxybenzyl)oxy]methyl}but-1-enyl)-2,2-dimethyl-1,3-dioxan-4-yl]pentanal

Guidance literature:: Multi-step reaction with 9 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

9.1: 76 percent / DIBALH / tetrahydrofuran / 3 h / -78 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; trimethylaluminum; titanium tetrachloride; diisobutylaluminium hydride; 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

: 912654-44-5
(2S)-2-[(4R,6R)-6-((1E)-1-{[(4-methoxybenzyl)oxy]methyl}but-1-enyl)-2,2-dimethyl-1,3-dioxan-4-yl]pentanal

Guidance literature:: Multi-step reaction with 10 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

10.1: 76 percent / DIBALH / tetrahydrofuran / 3 h / -78 °C

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