(2R,5R)-1-aza-2-(tert-butyl)-5-methoxycarbonyl-6,8-dioxo-7-[(Z)-1-hydroxy-3-(E)-(4’-methylphenyl)allylidene]-3-oxabicyclo[3.3.0]octane

Base Information

Chemical Name:(2R,5R)-1-aza-2-(tert-butyl)-5-methoxycarbonyl-6,8-dioxo-7-[(Z)-1-hydroxy-3-(E)-(4’-methylphenyl)allylidene]-3-oxabicyclo[3.3.0]octane
CAS No.:1571713-18-2
Molecular Formula:C₂₂H₂₅NO₆
Molecular Weight:399.444
Hs Code.:

Synonyms:(2R,5R)-1-aza-2-(tert-butyl)-5-methoxycarbonyl-6,8-dioxo-7-[(Z)-1-hydroxy-3-(E)-(4’-methylphenyl)allylidene]-3-oxabicyclo[3.3.0]octane

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Chemical Property of (2R,5R)-1-aza-2-(tert-butyl)-5-methoxycarbonyl-6,8-dioxo-7-[(Z)-1-hydroxy-3-(E)-(4’-methylphenyl)allylidene]-3-oxabicyclo[3.3.0]octane

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Technology Process of (2R,5R)-1-aza-2-(tert-butyl)-5-methoxycarbonyl-6,8-dioxo-7-[(Z)-1-hydroxy-3-(E)-(4’-methylphenyl)allylidene]-3-oxabicyclo[3.3.0]octane

There total 5 articles about (2R,5R)-1-aza-2-(tert-butyl)-5-methoxycarbonyl-6,8-dioxo-7-[(Z)-1-hydroxy-3-(E)-(4’-methylphenyl)allylidene]-3-oxabicyclo[3.3.0]octane 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: 75.0%

: 1571713-58-0
(2R,5R)-1-aza-2-(tert-butyl)-5-methoxycarbonyl-6,8-dioxo-7-[(Z)-1-hydroxy-1’-(diethylmethylphosphonate)allylidene]-3-oxabicyclo[3.3.0]octane,

: 104-87-0
4-methyl-benzaldehyde

: 1571713-18-2
(2R,5R)-1-aza-2-(tert-butyl)-5-methoxycarbonyl-6,8-dioxo-7-[(Z)-1-hydroxy-3-(E)-(4’-methylphenyl)allylidene]-3-oxabicyclo[3.3.0]octane

Guidance literature:: (2R,5R)-1-aza-2-(tert-butyl)-5-methoxycarbonyl-6,8-dioxo-7-[(Z)-1-hydroxy-1’-(diethylmethylphosphonate)allylidene]-3-oxabicyclo[3.3.0]octane,; With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 0.5h;

4-methyl-benzaldehyde; In tetrahydrofuran; at 0 ℃; for 0.166667h;
DOI:10.1039/c4ob00095a

Reference yield:

: 1571712-99-6
(2R,5R)-1-aza-2-(tert-butyl)-5-methoxycarbonyl-6,8-dioxo-7-[1-hydroxy-1’-methylvinylidene]-3-oxabicyclo[3.3.0]octane

: 104-87-0
4-methyl-benzaldehyde

: 1571713-18-2
(2R,5R)-1-aza-2-(tert-butyl)-5-methoxycarbonyl-6,8-dioxo-7-[(Z)-1-hydroxy-3-(E)-(4’-methylphenyl)allylidene]-3-oxabicyclo[3.3.0]octane

: 1571713-20-6
(2R,5R)-1-aza-2-(tert-butyl)-5-methoxycarbonyl-6,8-dioxo-7-[(E)-1-hydroxy-3-(E)-(4’-methylphenyl)allylidene]-3-oxabicyclo[3.3.0]octane

Guidance literature:: (2R,5R)-1-aza-2-(tert-butyl)-5-methoxycarbonyl-6,8-dioxo-7-[1-hydroxy-1’-methylvinylidene]-3-oxabicyclo[3.3.0]octane; With lithium diisopropyl amide; In tetrahydrofuran; at -10 ℃; for 1h;

4-methyl-benzaldehyde; In tetrahydrofuran; at -10 - 20 ℃; for 20h;
DOI:10.1039/c4ob00095a

Reference yield:

: 159970-77-1
(2R,5R)-1-aza-2-(tert-butyl)-5-methoxycarbonyl-6,8-dioxo-3-oxabicyclo[3.3.0]octane

: 1571713-18-2
(2R,5R)-1-aza-2-(tert-butyl)-5-methoxycarbonyl-6,8-dioxo-7-[(Z)-1-hydroxy-3-(E)-(4’-methylphenyl)allylidene]-3-oxabicyclo[3.3.0]octane

Guidance literature:: Multi-step reaction with 3 steps

1.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 20 °C

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C

2.2: 17 h / 0 - 20 °C

3.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C

3.2: 0.17 h / 0 °C

With dmap; potassium tert-butylate; sodium hydride; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; mineral oil; 3.1: |Horner-Wadsworth-Emmons Olefination / 3.2: |Horner-Wadsworth-Emmons Olefination;
DOI:10.1039/c4ob00095a