methyl (R,2Z,8E)-6-aza-10-bromo-5-isopropyl-6-(p-toluenesulfonyl)deca-2,8-dienoate

Base Information

Chemical Name:methyl (R,2Z,8E)-6-aza-10-bromo-5-isopropyl-6-(p-toluenesulfonyl)deca-2,8-dienoate
CAS No.:1254356-66-5
Molecular Formula:C₂₀H₂₈BrNO₄S
Molecular Weight:458.417
Hs Code.:

Synonyms:methyl (R,2Z,8E)-6-aza-10-bromo-5-isopropyl-6-(p-toluenesulfonyl)deca-2,8-dienoate

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Chemical Property of methyl (R,2Z,8E)-6-aza-10-bromo-5-isopropyl-6-(p-toluenesulfonyl)deca-2,8-dienoate

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Technology Process of methyl (R,2Z,8E)-6-aza-10-bromo-5-isopropyl-6-(p-toluenesulfonyl)deca-2,8-dienoate

There total 7 articles about methyl (R,2Z,8E)-6-aza-10-bromo-5-isopropyl-6-(p-toluenesulfonyl)deca-2,8-dienoate 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: 98.0%

: 1254356-63-2
methyl (R,2Z,8E)-6-aza-10-hydroxy-5-isopropyl-6-(p-toluenesulfonyl)deca-2,8-dienoate

: 1254356-66-5
methyl (R,2Z,8E)-6-aza-10-bromo-5-isopropyl-6-(p-toluenesulfonyl)deca-2,8-dienoate

Guidance literature:: With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0 ℃; for 4h; Reflux;
DOI:10.1021/jo101631y

Reference yield:

: 875438-79-2
(3R)-3-(p-toluenesulfonyl)amino-4-methylpentanenitrile

: 1254356-66-5
methyl (R,2Z,8E)-6-aza-10-bromo-5-isopropyl-6-(p-toluenesulfonyl)deca-2,8-dienoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: caesium carbonate / acetonitrile / 0.5 h / 20 °C

1.2: 12 h / 0 - 20 °C

2.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -78 °C

2.2: 0.25 h / -78 - 20 °C

3.1: 18-crown-6 ether; potassium hexamethylsilazane / tetrahydrofuran; toluene / 1 h / -78 °C

3.2: 3 h

4.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 4 h / 0 °C / Reflux

With 18-crown-6 ether; carbon tetrabromide; potassium hexamethylsilazane; diisobutylaluminium hydride; caesium carbonate; triphenylphosphine; In tetrahydrofuran; dichloromethane; toluene; acetonitrile; 3.2: Still-Gennari modified Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jo101631y

Reference yield:

: 1254356-58-5
(R,E)-8-acetoxy-4-aza-3-isopropyl-4-(p-toluenesulfonyl)oct-6-enenitrile

: 1254356-66-5
methyl (R,2Z,8E)-6-aza-10-bromo-5-isopropyl-6-(p-toluenesulfonyl)deca-2,8-dienoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -78 °C

1.2: 0.25 h / -78 - 20 °C

2.1: 18-crown-6 ether; potassium hexamethylsilazane / tetrahydrofuran; toluene / 1 h / -78 °C

2.2: 3 h

3.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 4 h / 0 °C / Reflux

With 18-crown-6 ether; carbon tetrabromide; potassium hexamethylsilazane; diisobutylaluminium hydride; triphenylphosphine; In tetrahydrofuran; dichloromethane; toluene; 2.2: Still-Gennari modified Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jo101631y