methyl (5R,Z)-6-aza-5-benzyl-8-bromo-8-phenyl-6-(p-toluenesulfonyl)oct-2-enoate

Base Information

Chemical Name:methyl (5R,Z)-6-aza-5-benzyl-8-bromo-8-phenyl-6-(p-toluenesulfonyl)oct-2-enoate
CAS No.:1254356-16-5
Molecular Formula:C₂₈H₃₀BrNO₄S
Molecular Weight:556.521
Hs Code.:

Synonyms:methyl (5R,Z)-6-aza-5-benzyl-8-bromo-8-phenyl-6-(p-toluenesulfonyl)oct-2-enoate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of methyl (5R,Z)-6-aza-5-benzyl-8-bromo-8-phenyl-6-(p-toluenesulfonyl)oct-2-enoate

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Technology Process of methyl (5R,Z)-6-aza-5-benzyl-8-bromo-8-phenyl-6-(p-toluenesulfonyl)oct-2-enoate

There total 7 articles about methyl (5R,Z)-6-aza-5-benzyl-8-bromo-8-phenyl-6-(p-toluenesulfonyl)oct-2-enoate 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: 50.0%

: 1254356-15-4
methyl (5R,Z)-6-aza-5-benzyl-8-hydroxy-8-phenyl-6-(p-toluenesulfonyl)oct-2-enoate

: 1254356-16-5
methyl (5R,Z)-6-aza-5-benzyl-8-bromo-8-phenyl-6-(p-toluenesulfonyl)oct-2-enoate

Guidance literature:: With phosphorus tribromide; In dichloromethane; at 0 - 20 ℃; for 1h; optical yield given as %de;
DOI:10.1021/jo101631y

Reference yield:

: 1254356-36-9
(3S)-4-aza-3-benzyl-6-oxo-6-phenyl-4-(p-toluenesulfonyl)hexanenitrile

: 1254356-16-5
methyl (5R,Z)-6-aza-5-benzyl-8-bromo-8-phenyl-6-(p-toluenesulfonyl)oct-2-enoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 °C / Inert atmosphere

1.2: 0.25 h / -78 - 20 °C / Inert atmosphere

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

2.2: 3 h

3.1: phosphorus tribromide / dichloromethane / 1 h / 0 - 20 °C

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

Reference yield:

: 1254356-39-2
(6S)-5-aza-6-benzyl-1-hydroxy-2-oxa-3-phenyl-5-(p-toluenesulfonyl)cycloheptane

: 1254356-16-5
methyl (5R,Z)-6-aza-5-benzyl-8-bromo-8-phenyl-6-(p-toluenesulfonyl)oct-2-enoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 18-crown-6 ether; potassium hexamethylsilazane / tetrahydrofuran; toluene / 1 h / -78 °C

1.2: 3 h

2.1: phosphorus tribromide / dichloromethane / 1 h / 0 - 20 °C

With 18-crown-6 ether; phosphorus tribromide; potassium hexamethylsilazane; In tetrahydrofuran; dichloromethane; toluene; 1.2: Still-Gennari modified Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jo101631y