2-methyl-but-(2E)-2-enoic acid [(5-hydroxy-3-(4R)-4-hydroxy-(2R)-2-methylheptyl)-2,4-dimethoxy-5-methoxymethoxy-phenyl]amide

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Chemical Name:2-methyl-but-(2E)-2-enoic acid [(5-hydroxy-3-(4R)-4-hydroxy-(2R)-2-methylheptyl)-2,4-dimethoxy-5-methoxymethoxy-phenyl]amide
CAS No.:622347-39-1
Molecular Formula:C₂₁H₃₃NO₅
Molecular Weight:379.497
Hs Code.:

Synonyms:2-methyl-but-(2E)-2-enoic acid [(5-hydroxy-3-(4R)-4-hydroxy-(2R)-2-methylheptyl)-2,4-dimethoxy-5-methoxymethoxy-phenyl]amide

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Chemical Property of 2-methyl-but-(2E)-2-enoic acid [(5-hydroxy-3-(4R)-4-hydroxy-(2R)-2-methylheptyl)-2,4-dimethoxy-5-methoxymethoxy-phenyl]amide

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Technology Process of 2-methyl-but-(2E)-2-enoic acid [(5-hydroxy-3-(4R)-4-hydroxy-(2R)-2-methylheptyl)-2,4-dimethoxy-5-methoxymethoxy-phenyl]amide

There total 15 articles about 2-methyl-but-(2E)-2-enoic acid [(5-hydroxy-3-(4R)-4-hydroxy-(2R)-2-methylheptyl)-2,4-dimethoxy-5-methoxymethoxy-phenyl]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: 65.0%

: 622347-38-0
(2E)-2-methyl-but-2-enoic acid {3-[(4R)-4-(tert-butyl-dimethyl-silanyloxy)-(2R)-2-methylheptyl]-2,4-dimethoxy-5-methoxymethoxy-phenyl}amide

: 622347-39-1
2-methyl-but-(2E)-2-enoic acid [(5-hydroxy-3-(4R)-4-hydroxy-(2R)-2-methylheptyl)-2,4-dimethoxy-5-methoxymethoxy-phenyl]amide

: (E)-2-Methyl-but-2-enoic acid {3-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-heptyl]-5-hydroxy-2,4-dimethoxy-phenyl}-amide

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 3h;
DOI:10.1021/ol035400g

Reference yield:

: 13330-65-9
2,4-dimethoxyphenol

: 622347-39-1
2-methyl-but-(2E)-2-enoic acid [(5-hydroxy-3-(4R)-4-hydroxy-(2R)-2-methylheptyl)-2,4-dimethoxy-5-methoxymethoxy-phenyl]amide

Guidance literature:: Multi-step reaction with 14 steps

1.1: 90 percent / NaH / dimethylformamide / 14 h / 0 - 20 °C

2.1: TMEDA; n-BuLi / tetrahydrofuran; hexane / 4 h / 20 °C

2.2: 70 percent / tetrahydrofuran; hexane / 1 h

3.1: 88 percent / NH₄NO₃; TFAA / acetonitrile / 0.2 h / 0 °C

4.1: 99 percent / NaBH₄ / tetrahydrofuran / 1 h / 20 °C

5.1: 88 percent / LiBr; NEt₃; MsCl / tetrahydrofuran / 2 h / 0 °C

6.1: 87 percent / NaHMDS / tetrahydrofuran / 4 h / -78 °C

7.1: 80 percent / LiBH₄ / diethyl ether / 1 h / 0 °C

8.1: 76 percent / PPh₃; DEAD / diethyl ether / 22 h / 20 °C

9.1: 72 percent / DIBAL-H / toluene / -78 - 20 °C

10.1: Ipc₂B(OMe) / diethyl ether / -78 - 20 °C

10.2: 82 percent / diethyl ether / 3 h / -78 °C

11.1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 - 20 °C

12.1: 88 percent / H₂ / Pd/C / ethanol / 5 h

13.1: 90 percent / NEt₃ / tetrahydrofuran / 1 h / 20 °C

14.1: 65 percent / aq. TFA / CH₂Cl₂ / 3 h / 20 °C

With ammonium nitrate; 2,6-dimethylpyridine; sodium tetrahydroborate; lithium borohydride; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; Ipc₂B(OMe); hydrogen; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; methanesulfonyl chloride; triethylamine; triphenylphosphine; trifluoroacetic acid; trifluoroacetic anhydride; lithium bromide; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/ol035400g

Reference yield:

: 613-45-6
2,4-Dimethoxybenzaldehyde

: 622347-39-1
2-methyl-but-(2E)-2-enoic acid [(5-hydroxy-3-(4R)-4-hydroxy-(2R)-2-methylheptyl)-2,4-dimethoxy-5-methoxymethoxy-phenyl]amide

Guidance literature:: Multi-step reaction with 15 steps

1.1: 78 percent / H₂O₂; H₂SO₄

2.1: 90 percent / NaH / dimethylformamide / 14 h / 0 - 20 °C

3.1: TMEDA; n-BuLi / tetrahydrofuran; hexane / 4 h / 20 °C

3.2: 70 percent / tetrahydrofuran; hexane / 1 h

4.1: 88 percent / NH₄NO₃; TFAA / acetonitrile / 0.2 h / 0 °C

5.1: 99 percent / NaBH₄ / tetrahydrofuran / 1 h / 20 °C

6.1: 88 percent / LiBr; NEt₃; MsCl / tetrahydrofuran / 2 h / 0 °C

7.1: 87 percent / NaHMDS / tetrahydrofuran / 4 h / -78 °C

8.1: 80 percent / LiBH₄ / diethyl ether / 1 h / 0 °C

9.1: 76 percent / PPh₃; DEAD / diethyl ether / 22 h / 20 °C

10.1: 72 percent / DIBAL-H / toluene / -78 - 20 °C

11.1: Ipc₂B(OMe) / diethyl ether / -78 - 20 °C

11.2: 82 percent / diethyl ether / 3 h / -78 °C

12.1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 - 20 °C

13.1: 88 percent / H₂ / Pd/C / ethanol / 5 h

14.1: 90 percent / NEt₃ / tetrahydrofuran / 1 h / 20 °C

15.1: 65 percent / aq. TFA / CH₂Cl₂ / 3 h / 20 °C

With ammonium nitrate; 2,6-dimethylpyridine; sodium tetrahydroborate; lithium borohydride; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; Ipc₂B(OMe); sulfuric acid; hydrogen; dihydrogen peroxide; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; methanesulfonyl chloride; triethylamine; triphenylphosphine; trifluoroacetic acid; trifluoroacetic anhydride; lithium bromide; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 1.1: Baeyer-Villiger oxidation;
DOI:10.1021/ol035400g