3-[3-((R)-1-{(3aS,6aR)-4-[(Z)-5-Azido-3-(4-methoxy-benzyloxymethyl)-pent-3-en-1-ynyl]-2,2-dimethyl-6,6a-dihydro-cyclopenta[1,3]dioxol-3a-yl}-prop-2-ynyloxy)-2-chloro-4-methoxy-phenyl]-propionic acid methyl ester

Base Information

• Chemical Name: 3-[3-((R)-1-{(3aS,6aR)-4-[(Z)-5-Azido-3-(4-methoxy-benzyloxymethyl)-pent-3-en-1-ynyl]-2,2-dimethyl-6,6a-dihydro-cyclopenta[1,3]dioxol-3a-yl}-prop-2-ynyloxy)-2-chloro-4-methoxy-phenyl]-propionic acid methyl ester
• CAS No.: 800374-66-7
• Molecular Formula: C₃₆H₃₈ClN₃O₈
• Molecular Weight: 676.166
• Mol file: 800374-66-7.mol

Synonyms:

Chemical Property of 3-[3-((R)-1-{(3aS,6aR)-4-[(Z)-5-Azido-3-(4-methoxy-benzyloxymethyl)-pent-3-en-1-ynyl]-2,2-dimethyl-6,6a-dihydro-cyclopenta[1,3]dioxol-3a-yl}-prop-2-ynyloxy)-2-chloro-4-methoxy-phenyl]-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[3-((R)-1-{(3aS,6aR)-4-[(Z)-5-Azido-3-(4-methoxy-benzyloxymethyl)-pent-3-en-1-ynyl]-2,2-dimethyl-6,6a-dihydro-cyclopenta[1,3]dioxol-3a-yl}-prop-2-ynyloxy)-2-chloro-4-methoxy-phenyl]-propionic acid methyl ester

There total 5 articles about 3-[3-((R)-1-{(3aS,6aR)-4-[(Z)-5-Azido-3-(4-methoxy-benzyloxymethyl)-pent-3-en-1-ynyl]-2,2-dimethyl-6,6a-dihydro-cyclopenta[1,3]dioxol-3a-yl}-prop-2-ynyloxy)-2-chloro-4-methoxy-phenyl]-propionic acid methyl ester 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:

3-[3-(tert-butyl-dimethyl-silanyloxy)-2-chloro-4-methoxy-phenyl]-acrylic acid methyl ester → 3-[3-((R)-1-{(3aS,6aR)-4-[(Z)-5-Azido-3-(4-methoxy-benzyloxymethyl)-pent-3-en-1-ynyl]-2,2-dimethyl-6,6a-dihydro-cyclopenta[1,3]dioxol-3a-yl}-prop-2-ynyloxy)-2-chloro-4-methoxy-phenyl]-propionic acid methyl ester (800374-66-7)

Guidance literature:

Multi-step reaction with 6 steps

1: H₂ / Pd/C / ethyl acetate / 10 h

2: TBAF / tetrahydrofuran / 0.5 h

3: 55 percent / CsF / dimethylformamide / 10 h / 60 °C

4: 90 percent / p-TsOH / 1 h / 20 °C

5: 89 percent / NaOMe / methanol / 6 h / 20 °C

6: 92 percent / NaN₃; PPh₃; CBr₄ / dimethylformamide / 1 h / 0 °C

With sodium azide; carbon tetrabromide; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; toluene-4-sulfonic acid; triphenylphosphine; cesium fluoride; palladium on activated charcoal; In tetrahydrofuran; methanol; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1055/s-2004-831314

Reference yield:

3-(2-chloro-3-hydroxy-4-methoxy-phenyl)-propionic acid methyl ester (800374-56-5) → 3-[3-((R)-1-{(3aS,6aR)-4-[(Z)-5-Azido-3-(4-methoxy-benzyloxymethyl)-pent-3-en-1-ynyl]-2,2-dimethyl-6,6a-dihydro-cyclopenta[1,3]dioxol-3a-yl}-prop-2-ynyloxy)-2-chloro-4-methoxy-phenyl]-propionic acid methyl ester (800374-66-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 55 percent / CsF / dimethylformamide / 10 h / 60 °C

2: 90 percent / p-TsOH / 1 h / 20 °C

3: 89 percent / NaOMe / methanol / 6 h / 20 °C

4: 92 percent / NaN₃; PPh₃; CBr₄ / dimethylformamide / 1 h / 0 °C

With sodium azide; carbon tetrabromide; sodium methylate; toluene-4-sulfonic acid; triphenylphosphine; cesium fluoride; In methanol; N,N-dimethyl-formamide;

DOI:10.1055/s-2004-831314

Reference yield:

3-[3-(tert-butyl-dimethyl-silanyloxy)-2-chloro-4-methoxy-phenyl]-propionic acid methyl ester → 3-[3-((R)-1-{(3aS,6aR)-4-[(Z)-5-Azido-3-(4-methoxy-benzyloxymethyl)-pent-3-en-1-ynyl]-2,2-dimethyl-6,6a-dihydro-cyclopenta[1,3]dioxol-3a-yl}-prop-2-ynyloxy)-2-chloro-4-methoxy-phenyl]-propionic acid methyl ester (800374-66-7)

Guidance literature:

Multi-step reaction with 5 steps

1: TBAF / tetrahydrofuran / 0.5 h

2: 55 percent / CsF / dimethylformamide / 10 h / 60 °C

3: 90 percent / p-TsOH / 1 h / 20 °C

4: 89 percent / NaOMe / methanol / 6 h / 20 °C

5: 92 percent / NaN₃; PPh₃; CBr₄ / dimethylformamide / 1 h / 0 °C

With sodium azide; carbon tetrabromide; tetrabutyl ammonium fluoride; sodium methylate; toluene-4-sulfonic acid; triphenylphosphine; cesium fluoride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1055/s-2004-831314

upstream raw materials:

3-(2-chloro-3-hydroxy-4-methoxy-phenyl)-propionic acid methyl ester

2,2-Dimethyl-propionic acid (Z)-5-((3aS,6aR)-3a-{(R)-1-[2-chloro-6-methoxy-3-(2-methoxycarbonyl-ethyl)-phenoxy]-prop-2-ynyl}-2,2-dimethyl-6,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl)-3-(4-methoxy-benzyloxymethyl)-pent-2-en-4-ynyl ester

2,2-Dimethyl-propionic acid (Z)-5-((4R,5S)-5-{(R)-1-[2-chloro-6-methoxy-3-(2-methoxycarbonyl-ethyl)-phenoxy]-prop-2-ynyl}-4,5-dihydroxy-cyclopent-1-enyl)-3-(4-methoxy-benzyloxymethyl)-pent-2-en-4-ynyl ester

Downstream raw materials:

C₃₅H₃₆ClNO₇

C₃₅H₃₅ClINO₇

3-[3-((R)-1-{(3aS,6aR)-4-[(Z)-5-Azido-3-(4-methoxy-benzyloxymethyl)-pent-3-en-1-ynyl]-2,2-dimethyl-6,6a-dihydro-cyclopenta[1,3]dioxol-3a-yl}-prop-2-ynyloxy)-2-chloro-4-methoxy-phenyl]-propionic acid pentafluorophenyl ester