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

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 pentafluorophenyl ester
• CAS No.: 800374-58-7
• Molecular Formula: C₄₁H₃₅ClF₅N₃O₈
• Molecular Weight: 828.189
• Mol file: 800374-58-7.mol

Synonyms: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

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 pentafluorophenyl 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 pentafluorophenyl ester

There total 8 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 pentafluorophenyl 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 pentafluorophenyl ester (800374-58-7)

Guidance literature:

Multi-step reaction with 8 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

7: aq. LiOH / tetrahydrofuran / 10 h / 20 °C

8: EDC; DMAP / CH₂Cl₂ / 20 °C

With dmap; lithium hydroxide; sodium azide; carbon tetrabromide; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; toluene-4-sulfonic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triphenylphosphine; cesium fluoride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1055/s-2004-831314

Reference yield:

2,3,4,5,6-pentafluorophenol (771-61-9) + 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 → 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 (800374-58-7)

Guidance literature:

With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; at 20 ℃;

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 pentafluorophenyl ester (800374-58-7)

Guidance literature:

Multi-step reaction with 6 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

5: aq. LiOH / tetrahydrofuran / 10 h / 20 °C

6: EDC; DMAP / CH₂Cl₂ / 20 °C

With dmap; lithium hydroxide; sodium azide; carbon tetrabromide; sodium methylate; toluene-4-sulfonic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triphenylphosphine; cesium fluoride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1055/s-2004-831314

upstream raw materials:

2,3,4,5,6-pentafluorophenol

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

3-[2-Chloro-3-((R)-1-{(3aS,6aR)-4-[(Z)-5-hydroxy-3-(4-methoxy-benzyloxymethyl)-pent-3-en-1-ynyl]-2,2-dimethyl-6,6a-dihydro-cyclopenta[1,3]dioxol-3a-yl}-prop-2-ynyloxy)-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

Downstream raw materials:

C₃₅H₃₅ClINO₇

C₃₅H₃₆ClNO₇