(R)-2-(4-{(2S,3R,4R,5S)-5-[4-((1R,2R)-2-Benzo[1,3]dioxol-5-yl-2-hydroxy-1-methyl-ethoxy)-3-methoxy-phenyl]-3,4-dimethyl-tetrahydro-furan-2-yl}-2-methoxy-phenoxy)-N-methoxy-N-methyl-propionamide

Base Information

• Chemical Name: (R)-2-(4-{(2S,3R,4R,5S)-5-[4-((1R,2R)-2-Benzo[1,3]dioxol-5-yl-2-hydroxy-1-methyl-ethoxy)-3-methoxy-phenyl]-3,4-dimethyl-tetrahydro-furan-2-yl}-2-methoxy-phenoxy)-N-methoxy-N-methyl-propionamide
• CAS No.: 915158-88-2
• Molecular Formula: C₃₅H₄₃NO₁₀
• Molecular Weight: 637.727
• Mol file: 915158-88-2.mol

Synonyms:(R)-2-(4-{(2S,3R,4R,5S)-5-[4-((1R,2R)-2-Benzo[1,3]dioxol-5-yl-2-hydroxy-1-methyl-ethoxy)-3-methoxy-phenyl]-3,4-dimethyl-tetrahydro-furan-2-yl}-2-methoxy-phenoxy)-N-methoxy-N-methyl-propionamide

Chemical Property of (R)-2-(4-{(2S,3R,4R,5S)-5-[4-((1R,2R)-2-Benzo[1,3]dioxol-5-yl-2-hydroxy-1-methyl-ethoxy)-3-methoxy-phenyl]-3,4-dimethyl-tetrahydro-furan-2-yl}-2-methoxy-phenoxy)-N-methoxy-N-methyl-propionamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-(4-{(2S,3R,4R,5S)-5-[4-((1R,2R)-2-Benzo[1,3]dioxol-5-yl-2-hydroxy-1-methyl-ethoxy)-3-methoxy-phenyl]-3,4-dimethyl-tetrahydro-furan-2-yl}-2-methoxy-phenoxy)-N-methoxy-N-methyl-propionamide

There total 10 articles about (R)-2-(4-{(2S,3R,4R,5S)-5-[4-((1R,2R)-2-Benzo[1,3]dioxol-5-yl-2-hydroxy-1-methyl-ethoxy)-3-methoxy-phenyl]-3,4-dimethyl-tetrahydro-furan-2-yl}-2-methoxy-phenoxy)-N-methoxy-N-methyl-propionamide 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: 92.0%

(R)-2-(4-{(2S,3R,4R,5S)-5-[4-((1R,2R)-2-Benzo[1,3]dioxol-5-yl-2-hydroxy-1-methyl-ethoxy)-3-methoxy-phenyl]-3,4-dimethyl-tetrahydro-furan-2-yl}-2-methoxy-phenoxy)-propionic acid methyl ester (915158-72-4) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → (R)-2-(4-{(2S,3R,4R,5S)-5-[4-((1R,2R)-2-Benzo[1,3]dioxol-5-yl-2-hydroxy-1-methyl-ethoxy)-3-methoxy-phenyl]-3,4-dimethyl-tetrahydro-furan-2-yl}-2-methoxy-phenoxy)-N-methoxy-N-methyl-propionamide (915158-88-2)

Guidance literature:

With dimethylaluminum chloride; In hexane; dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/ol0621710

Reference yield:

4-[(2S,3R,4R,5S)-5-(4-Benzyloxy-3-methoxy-phenyl)-3,4-dimethyl-tetrahydro-furan-2-yl]-2-methoxy-phenol (915158-67-7) → (R)-2-(4-{(2S,3R,4R,5S)-5-[4-((1R,2R)-2-Benzo[1,3]dioxol-5-yl-2-hydroxy-1-methyl-ethoxy)-3-methoxy-phenyl]-3,4-dimethyl-tetrahydro-furan-2-yl}-2-methoxy-phenoxy)-N-methoxy-N-methyl-propionamide (915158-88-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 92 percent / BEMP / CH₂Cl₂ / -45 - 0 °C

2: 95 percent / Me₂AlCl / CH₂Cl₂; hexane / 1 h / 20 °C

3: 90 percent / tetrahydrofuran / 1 h / -30 °C

4: 77 percent / Amberlite IRA-400-supported borohydride / methanol / 16 h / 20 °C

5: 96 percent / H₂ / Pd(OH)2/C / ethyl acetate / 2 h / 20 °C

6: 92 percent / BEMP / CH₂Cl₂ / 0.67 h / -45 °C

7: 92 percent / Me₂AlCl / CH₂Cl₂; hexane / 1 h / 20 °C

With Amberlite IRA-400-supported borohydride; hydrogen; dimethylaluminum chloride; 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine; palladium dihydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate;

DOI:10.1021/ol0621710

Reference yield:

(R)-2-{4-[(2S,3R,4R,5S)-5-(4-Benzyloxy-3-methoxy-phenyl)-3,4-dimethyl-tetrahydro-furan-2-yl]-2-methoxy-phenoxy}-propionic acid methyl ester (915158-70-2) → (R)-2-(4-{(2S,3R,4R,5S)-5-[4-((1R,2R)-2-Benzo[1,3]dioxol-5-yl-2-hydroxy-1-methyl-ethoxy)-3-methoxy-phenyl]-3,4-dimethyl-tetrahydro-furan-2-yl}-2-methoxy-phenoxy)-N-methoxy-N-methyl-propionamide (915158-88-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 95 percent / Me₂AlCl / CH₂Cl₂; hexane / 1 h / 20 °C

2: 90 percent / tetrahydrofuran / 1 h / -30 °C

3: 77 percent / Amberlite IRA-400-supported borohydride / methanol / 16 h / 20 °C

4: 96 percent / H₂ / Pd(OH)2/C / ethyl acetate / 2 h / 20 °C

5: 92 percent / BEMP / CH₂Cl₂ / 0.67 h / -45 °C

6: 92 percent / Me₂AlCl / CH₂Cl₂; hexane / 1 h / 20 °C

With Amberlite IRA-400-supported borohydride; hydrogen; dimethylaluminum chloride; 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine; palladium dihydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate;

DOI:10.1021/ol0621710

upstream raw materials:

(R)-2-(4-{(2S,3R,4R,5S)-5-[4-((1R,2R)-2-Benzo[1,3]dioxol-5-yl-2-hydroxy-1-methyl-ethoxy)-3-methoxy-phenyl]-3,4-dimethyl-tetrahydro-furan-2-yl}-2-methoxy-phenoxy)-propionic acid methyl ester

N,O-dimethylhydroxylamine*hydrochloride

4-[(2S,3R,4R,5S)-5-(4-Benzyloxy-3-methoxy-phenyl)-3,4-dimethyl-tetrahydro-furan-2-yl]-2-methoxy-phenol

(R)-2-{4-[(2S,3R,4R,5S)-5-(4-Benzyloxy-3-methoxy-phenyl)-3,4-dimethyl-tetrahydro-furan-2-yl]-2-methoxy-phenoxy}-propionic acid methyl ester