2-(allyloxy)-6-((1S,2R,3R)-1,2-dihydroxy-3-methylpent-4-en-1-yl)-N,N-diisopropyl-3-methylbenzamide

Base Information

• Chemical Name: 2-(allyloxy)-6-((1S,2R,3R)-1,2-dihydroxy-3-methylpent-4-en-1-yl)-N,N-diisopropyl-3-methylbenzamide
• CAS No.: 1412443-99-2
• Molecular Formula: C₂₃H₃₅NO₄
• Molecular Weight: 389.535
• Mol file: 1412443-99-2.mol

Synonyms:2-(allyloxy)-6-((1S,2R,3R)-1,2-dihydroxy-3-methylpent-4-en-1-yl)-N,N-diisopropyl-3-methylbenzamide

Chemical Property of 2-(allyloxy)-6-((1S,2R,3R)-1,2-dihydroxy-3-methylpent-4-en-1-yl)-N,N-diisopropyl-3-methylbenzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(allyloxy)-6-((1S,2R,3R)-1,2-dihydroxy-3-methylpent-4-en-1-yl)-N,N-diisopropyl-3-methylbenzamide

There total 13 articles about 2-(allyloxy)-6-((1S,2R,3R)-1,2-dihydroxy-3-methylpent-4-en-1-yl)-N,N-diisopropyl-3-methylbenzamide 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: 93.0%

2-(allyloxy)-6-((1S,2R,3R)-2-((tert-butyldimethylsilyl)oxy)-1-hydroxy-3-methylpent-4-en-1-yl)-N,N-diisopropyl-3-methylbenzamide → 2-(allyloxy)-6-((1S,2R,3R)-1,2-dihydroxy-3-methylpent-4-en-1-yl)-N,N-diisopropyl-3-methylbenzamide (1412443-99-2)

Guidance literature:

With tris(dimethylamino)sulfonium trimethylsilyldifluoride; In water; N,N-dimethyl-formamide; for 14h;

DOI:10.1021/acs.joc.5b02781

Reference yield:

ethyl (2R,3R)-2-((tert-Butyldimethylsilyl)oxy)-3-methylpent-4-enoate → 2-(allyloxy)-6-((1S,2R,3R)-1,2-dihydroxy-3-methylpent-4-en-1-yl)-N,N-diisopropyl-3-methylbenzamide (1412443-99-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: diisobutylaluminium hydride / dichloromethane / 12.5 h / -78 - 20 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

2.2: 2 h / -78 - 20 °C / Inert atmosphere

3.1: tert.-butyl lithium / tetrahydrofuran; pentane / 0.08 h / -90 °C / Inert atmosphere

3.2: 0.75 h / -90 °C / Inert atmosphere

4.1: tris(dimethylamino)sulfonium trimethylsilyldifluoride / water; N,N-dimethyl-formamide / 14 h

With oxalyl dichloride; tris(dimethylamino)sulfonium trimethylsilyldifluoride; tert.-butyl lithium; diisobutylaluminium hydride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; pentane; 2.1: |Swern Oxidation / 2.2: |Swern Oxidation;

DOI:10.1021/acs.joc.5b02781

Reference yield:

N,N-diisopropyl-2-methoxy-3-methylbenzamide → 2-(allyloxy)-6-((1S,2R,3R)-1,2-dihydroxy-3-methylpent-4-en-1-yl)-N,N-diisopropyl-3-methylbenzamide (1412443-99-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: magnesium; iodine / diethyl ether; toluene / 12 h / Reflux; Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / Cooling with ice; Inert atmosphere

2.2: 3 h / 20 °C / Inert atmosphere

3.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / tetrahydrofuran; hexane / 0.58 h / -78 °C / Inert atmosphere

3.2: 1.5 h / -78 °C / Inert atmosphere

4.1: tert.-butyl lithium / tetrahydrofuran; pentane / 0.08 h / -90 °C / Inert atmosphere

4.2: 0.75 h / -90 °C / Inert atmosphere

5.1: tris(dimethylamino)sulfonium trimethylsilyldifluoride / water; N,N-dimethyl-formamide / 14 h

With N,N,N,N,-tetramethylethylenediamine; tris(dimethylamino)sulfonium trimethylsilyldifluoride; iodine; tert.-butyl lithium; sec.-butyllithium; sodium hydride; magnesium; In tetrahydrofuran; diethyl ether; hexane; water; N,N-dimethyl-formamide; toluene; mineral oil; pentane;

DOI:10.1021/acs.joc.5b02781

upstream raw materials:

3-methylsalicylic acid

2-(allyloxy)-N,N-diisopropyl-3-methylbenzamide

methyl 2-methoxy-3-methylbenzoate

2-methoxy-3-methylbenzoic acid