ethyl 2-((R,4E,6E)-N-(2,4-dimethoxybenzyl)-6-methyl-3-oxo-8-((1R,3R,4S,5R)-1,4,8-tri-methyl-2,9-dioxabicyclo[3.3.1]non-7-en-3-yl)nona-4,6-dienamido)acetate

Base Information

• Chemical Name: ethyl 2-((R,4E,6E)-N-(2,4-dimethoxybenzyl)-6-methyl-3-oxo-8-((1R,3R,4S,5R)-1,4,8-tri-methyl-2,9-dioxabicyclo[3.3.1]non-7-en-3-yl)nona-4,6-dienamido)acetate
• CAS No.: 1403660-73-0
• Molecular Formula: C₃₃H₄₅NO₈
• Molecular Weight: 583.722
• Mol file: 1403660-73-0.mol

Synonyms:ethyl 2-((R,4E,6E)-N-(2,4-dimethoxybenzyl)-6-methyl-3-oxo-8-((1R,3R,4S,5R)-1,4,8-tri-methyl-2,9-dioxabicyclo[3.3.1]non-7-en-3-yl)nona-4,6-dienamido)acetate

Chemical Property of ethyl 2-((R,4E,6E)-N-(2,4-dimethoxybenzyl)-6-methyl-3-oxo-8-((1R,3R,4S,5R)-1,4,8-tri-methyl-2,9-dioxabicyclo[3.3.1]non-7-en-3-yl)nona-4,6-dienamido)acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2-((R,4E,6E)-N-(2,4-dimethoxybenzyl)-6-methyl-3-oxo-8-((1R,3R,4S,5R)-1,4,8-tri-methyl-2,9-dioxabicyclo[3.3.1]non-7-en-3-yl)nona-4,6-dienamido)acetate

There total 14 articles about ethyl 2-((R,4E,6E)-N-(2,4-dimethoxybenzyl)-6-methyl-3-oxo-8-((1R,3R,4S,5R)-1,4,8-tri-methyl-2,9-dioxabicyclo[3.3.1]non-7-en-3-yl)nona-4,6-dienamido)acetate 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: 99.0%

2,2-dimethyl-6-((R,1E,3E)-3-methyl-5-((1R,3R,4S,5R)-1,4,8-trimethyl-2,9-dioxabicyclo[3.3.1]non-7-en-3-yl)hexa-1,3-dienyl)-4H-1,3-dioxin-4-one (1403660-58-1) + ethyl 2-{[(2,4-dimethoxyphenyl)methyl]amino}acetate (95218-34-1) → ethyl 2-((R,4E,6E)-N-(2,4-dimethoxybenzyl)-6-methyl-3-oxo-8-((1R,3R,4S,5R)-1,4,8-tri-methyl-2,9-dioxabicyclo[3.3.1]non-7-en-3-yl)nona-4,6-dienamido)acetate (1403660-73-0)

Guidance literature:

In toluene; at 110 ℃; for 6h; Inert atmosphere;

DOI:10.1021/jo3016709

Reference yield:

C17H30O5 (1403660-63-8) → ethyl 2-((R,4E,6E)-N-(2,4-dimethoxybenzyl)-6-methyl-3-oxo-8-((1R,3R,4S,5R)-1,4,8-tri-methyl-2,9-dioxabicyclo[3.3.1]non-7-en-3-yl)nona-4,6-dienamido)acetate (1403660-73-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: potassium hexamethylsilazane; 18-crown-6 ether / tetrahydrofuran; toluene / 0.5 h / -78 °C / Inert atmosphere

1.2: 5 h / -78 - 20 °C

2.1: camphor-10-sulfonic acid / methanol / 2 h / 20 °C

3.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / 0 °C

4.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 1 h / 0 - 20 °C

5.1: toluene / 12 h / 110 °C

6.1: diisobutylaluminium hydride / dichloromethane; toluene / 3 h / 0 °C

7.1: [bis(acetoxy)iodo]benzene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane / 1 h / 20 °C

8.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere

8.2: 12 h / 0 - 20 °C / Inert atmosphere

9.1: toluene / 6 h / 110 °C / Inert atmosphere

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 18-crown-6 ether; [bis(acetoxy)iodo]benzene; camphor-10-sulfonic acid; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; methanol; dichloromethane; toluene; mineral oil; 1.1: |Still-Gennary Z-Olefination / 1.2: |Still-Gennary Z-Olefination / 5.1: |Wittig Olefination / 8.1: |Horner-Wadsworth-Emmons Olefination / 8.2: |Horner-Wadsworth-Emmons Olefination;

DOI:10.1021/jo3016709

Reference yield:

(R)-2-((4R,5S,6R)-2,2,5-trimethyl-6-((Z)-3-methyl-4-oxopent-2-enyl)-1,3-dioxan-4-yl)propyl pivalate (1403660-61-6) → ethyl 2-((R,4E,6E)-N-(2,4-dimethoxybenzyl)-6-methyl-3-oxo-8-((1R,3R,4S,5R)-1,4,8-tri-methyl-2,9-dioxabicyclo[3.3.1]non-7-en-3-yl)nona-4,6-dienamido)acetate (1403660-73-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: camphor-10-sulfonic acid / methanol / 2 h / 20 °C

2.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / 0 °C

3.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 1 h / 0 - 20 °C

4.1: toluene / 12 h / 110 °C

5.1: diisobutylaluminium hydride / dichloromethane; toluene / 3 h / 0 °C

6.1: [bis(acetoxy)iodo]benzene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane / 1 h / 20 °C

7.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere

7.2: 12 h / 0 - 20 °C / Inert atmosphere

8.1: toluene / 6 h / 110 °C / Inert atmosphere

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; camphor-10-sulfonic acid; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; methanol; dichloromethane; toluene; mineral oil; 4.1: |Wittig Olefination / 7.1: |Horner-Wadsworth-Emmons Olefination / 7.2: |Horner-Wadsworth-Emmons Olefination;

DOI:10.1021/jo3016709

upstream raw materials:

C₁₇H₃₀O₅

(R)-2-((4R,5S,6R)-2,2,5-trimethyl-6-((Z)-3-methyl-4-oxopent-2-enyl)-1,3-dioxan-4-yl)propyl pivalate

(R)-2-((1R,3R,4S,5R)-1,4,8-trimethyl-2,9-dioxabicyclo[3.3.1]non-7-en-3-yl)propyl pivalate

(R)-2-((1R,3R,4S,5R)-1,4,8-trimethyl-2,9-dioxabicyclo[3.3.1]non-7-en-3-yl)propan-1-ol