2-(allyloxy)-6-((1S,2R,3R)-1-hydroxy-3-methyl-2-(triethylsilyloxy)hex-5-enyl)-N,Ndiisopropyl-3-methylbenzamide

Base Information

Chemical Name:2-(allyloxy)-6-((1S,2R,3R)-1-hydroxy-3-methyl-2-(triethylsilyloxy)hex-5-enyl)-N,Ndiisopropyl-3-methylbenzamide
CAS No.:1412443-75-4
Molecular Formula:C₃₀H₅₁NO₄Si
Molecular Weight:517.825
Hs Code.:

Synonyms:2-(allyloxy)-6-((1S,2R,3R)-1-hydroxy-3-methyl-2-(triethylsilyloxy)hex-5-enyl)-N,Ndiisopropyl-3-methylbenzamide

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Chemical Property of 2-(allyloxy)-6-((1S,2R,3R)-1-hydroxy-3-methyl-2-(triethylsilyloxy)hex-5-enyl)-N,Ndiisopropyl-3-methylbenzamide

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Technology Process of 2-(allyloxy)-6-((1S,2R,3R)-1-hydroxy-3-methyl-2-(triethylsilyloxy)hex-5-enyl)-N,Ndiisopropyl-3-methylbenzamide

There total 10 articles about 2-(allyloxy)-6-((1S,2R,3R)-1-hydroxy-3-methyl-2-(triethylsilyloxy)hex-5-enyl)-N,Ndiisopropyl-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: 80.0%

: 1412443-74-3
(2R,3R)-3-methyl-2-((triethylsilyl)oxy)hex-5-enal

: (R)-2-(allyloxy)-N,N-diisopropyl-3-methyl-6-(p-tolylsulfinyl)benzamide

: 1412443-75-4
2-(allyloxy)-6-((1S,2R,3R)-1-hydroxy-3-methyl-2-(triethylsilyloxy)hex-5-enyl)-N,Ndiisopropyl-3-methylbenzamide

Guidance literature:: (R)-2-(allyloxy)-N,N-diisopropyl-3-methyl-6-(p-tolylsulfinyl)benzamide; With tert.-butyl lithium; In tetrahydrofuran; pentane; at -90 ℃; for 0.0833333h;

(2R,3R)-3-methyl-2-((triethylsilyl)oxy)hex-5-enal; In tetrahydrofuran; pentane; at -78 ℃; for 1h;
DOI:10.1021/ja309685n

Reference yield:

: 2-allyloxy-3-methyl-benzoyl chloride

: 1412443-75-4
2-(allyloxy)-6-((1S,2R,3R)-1-hydroxy-3-methyl-2-(triethylsilyloxy)hex-5-enyl)-N,Ndiisopropyl-3-methylbenzamide

Guidance literature:: Multi-step reaction with 3 steps

1.1: dichloromethane / 12 h / 20 °C

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

2.2: 1.5 h

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

3.2: 1 h / -78 °C

With N,N,N,N,-tetramethylethylenediamine; tert.-butyl lithium; sec.-butyllithium; In tetrahydrofuran; hexane; dichloromethane; pentane;
DOI:10.1021/ja309685n

Reference yield:

: 154550-06-8
allyl 2-(allyloxy)-3-methylbenzoate

: 1412443-75-4
2-(allyloxy)-6-((1S,2R,3R)-1-hydroxy-3-methyl-2-(triethylsilyloxy)hex-5-enyl)-N,Ndiisopropyl-3-methylbenzamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium hydroxide / methanol; water / 4 h / Reflux

2.1: thionyl chloride / dichloromethane / 6 h / Reflux

3.1: dichloromethane / 12 h / 20 °C

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

4.2: 1.5 h

5.1: tert.-butyl lithium / tetrahydrofuran; pentane / 0.08 h / -90 °C

5.2: 1 h / -78 °C

With thionyl chloride; N,N,N,N,-tetramethylethylenediamine; tert.-butyl lithium; sec.-butyllithium; sodium hydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; pentane;
DOI:10.1021/ja309685n