(E)-(2R,3R)-3-Hydroxy-2,4-dimethyl-hept-4-enoic acid methoxy-methyl-amide

Base Information

• Chemical Name: (E)-(2R,3R)-3-Hydroxy-2,4-dimethyl-hept-4-enoic acid methoxy-methyl-amide
• CAS No.: 541511-47-1
• Molecular Formula: C₁₁H₂₁NO₃
• Molecular Weight: 215.293
• Mol file: 541511-47-1.mol

Synonyms:(E)-(2R,3R)-3-Hydroxy-2,4-dimethyl-hept-4-enoic acid methoxy-methyl-amide

Chemical Property of (E)-(2R,3R)-3-Hydroxy-2,4-dimethyl-hept-4-enoic acid methoxy-methyl-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(2R,3R)-3-Hydroxy-2,4-dimethyl-hept-4-enoic acid methoxy-methyl-amide

There total 1 articles about (E)-(2R,3R)-3-Hydroxy-2,4-dimethyl-hept-4-enoic acid methoxy-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: 100.0%

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + (4R,5S)-3-((E)-(2R,3R)-3-Hydroxy-2,4-dimethyl-hept-4-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one (779353-80-9) → (E)-(2R,3R)-3-Hydroxy-2,4-dimethyl-hept-4-enoic acid methoxy-methyl-amide (541511-47-1) + 4-methyl-5-phenyloxazolidin-2-one (77943-39-6)

Guidance literature:

N,O-dimethylhydroxylamine*hydrochloride; With trimethylaluminum; In tetrahydrofuran; toluene; at 0 - 20 ℃;

(4R,5S)-3-((E)-(2R,3R)-3-Hydroxy-2,4-dimethyl-hept-4-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one; In tetrahydrofuran; toluene; at 0 ℃; for 1h;

DOI:10.1016/j.tet.2004.06.125

Reference yield:

(E)-(2R,3R)-3-Hydroxy-2,4-dimethyl-hept-4-enoic acid methoxy-methyl-amide (541511-47-1) → C35H35Br3O6

Guidance literature:

Multi-step reaction with 14 steps

1: 100 percent / imidazole / dimethylformamide / 0.75 h / 20 °C

2: 91 percent / DIBAL / tetrahydrofuran; hexane / 2 h / -78 °C

3: 40 percent / lithium diisopropylamide / tetrahydrofuran / 0.75 h / -78 °C

4: 95 percent / imidazole / dimethylformamide / 1.5 h / 20 °C

5: 93 percent / DIBAL / CH₂Cl₂; hexane / 2 h / -23 °C

6: 84 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 °C

7: 86 percent / NaH / 1,2-dimethoxy-ethane / 1 h / -10 °C

8: 98 percent / HF*pyridine; pyridine / tetrahydrofuran / 0.67 h / 20 °C

9: 60 percent / MnO₂ / CH₂Cl₂ / 12 h / 20 °C

10: 89 percent / imidazole / dimethylformamide / 2 h / 20 °C

11: CeCl₃*7H₂O; NaBH₄ / ethanol / -78 - -23 °C

12: HF*pyridine; pyridine / tetrahydrofuran / 0.5 h / 20 °C

13: DIBAL / CH₂Cl₂; hexane / 1.5 h / -23 °C

14: 1.2 mg / pyridine / 12 h / 20 °C

With pyridine; 1H-imidazole; manganese(IV) oxide; sodium tetrahydroborate; cerium(III) chloride; oxalyl dichloride; sodium hydride; diisobutylaluminium hydride; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; 6: Swern oxidation / 7: Horner-Emmons reaction;

DOI:10.1016/j.tet.2004.06.125

Reference yield:

(E)-(2R,3R)-3-Hydroxy-2,4-dimethyl-hept-4-enoic acid methoxy-methyl-amide (541511-47-1) → C35H35Br3O6

Guidance literature:

Multi-step reaction with 14 steps

1: 100 percent / imidazole / dimethylformamide / 0.75 h / 20 °C

2: 91 percent / DIBAL / tetrahydrofuran; hexane / 2 h / -78 °C

3: 58 percent / lithium diisopropylamide / tetrahydrofuran / 0.75 h / -78 °C

4: 99 percent / imidazole / dimethylformamide / 1.5 h / 20 °C

5: 94 percent / DIBAL / CH₂Cl₂; hexane / 2 h / -23 °C

6: 75 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 °C

7: 88 percent / NaH / 1,2-dimethoxy-ethane / 1 h / -10 °C

8: 98 percent / HF*pyridine; pyridine / tetrahydrofuran / 0.67 h / 20 °C

9: 69 percent / MnO₂ / CH₂Cl₂ / 12 h / 20 °C

10: 85 percent / imidazole / dimethylformamide / 2 h / 20 °C

11: CeCl₃*7H₂O; NaBH₄ / ethanol / -78 - -23 °C

12: HF*pyridine; pyridine / tetrahydrofuran / 0.5 h / 20 °C

13: DIBAL / CH₂Cl₂; hexane / 1.5 h / -23 °C

14: 5.5 mg / pyridine / 12 h / 20 °C

With pyridine; 1H-imidazole; manganese(IV) oxide; sodium tetrahydroborate; cerium(III) chloride; oxalyl dichloride; sodium hydride; diisobutylaluminium hydride; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; 6: Swern oxidation / 7: Horner-Emmons reaction;

DOI:10.1016/j.tet.2004.06.125

upstream raw materials:

N,O-dimethylhydroxylamine*hydrochloride

(4R,5S)-3-((E)-(2R,3R)-3-Hydroxy-2,4-dimethyl-hept-4-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one

Refernces