3-((p-bromobenzenesulfonyl)oxy)-3a-acetoxy-4-(benzyloxy)-6-methoxy-2,3,3a,8a-tetrahydrofuro<2,3-b>benzofuran

Base Information

• Chemical Name: 3-((p-bromobenzenesulfonyl)oxy)-3a-acetoxy-4-(benzyloxy)-6-methoxy-2,3,3a,8a-tetrahydrofuro<2,3-b>benzofuran
• CAS No.: 78596-82-4
• Molecular Formula: C₂₆H₂₃BrO₉S
• Molecular Weight: 591.433
• Mol file: 78596-82-4.mol

Synonyms:3-((p-bromobenzenesulfonyl)oxy)-3a-acetoxy-4-(benzyloxy)-6-methoxy-2,3,3a,8a-tetrahydrofuro<2,3-b>benzofuran

Chemical Property of 3-((p-bromobenzenesulfonyl)oxy)-3a-acetoxy-4-(benzyloxy)-6-methoxy-2,3,3a,8a-tetrahydrofuro<2,3-b>benzofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-((p-bromobenzenesulfonyl)oxy)-3a-acetoxy-4-(benzyloxy)-6-methoxy-2,3,3a,8a-tetrahydrofuro<2,3-b>benzofuran

There total 11 articles about 3-((p-bromobenzenesulfonyl)oxy)-3a-acetoxy-4-(benzyloxy)-6-methoxy-2,3,3a,8a-tetrahydrofuro<2,3-b>benzofuran 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: 100.0%

acetic anhydride (108-24-7) + 3-((p-bromobenzenesulfonyl)oxy)-3a-hydroxy-4-(benzyloxy)-6-methoxy-2,3,3a,8a-tetrahydrofuro<2,3-b>benzofuran (78596-81-3) → 3-((p-bromobenzenesulfonyl)oxy)-3a-acetoxy-4-(benzyloxy)-6-methoxy-2,3,3a,8a-tetrahydrofuro<2,3-b>benzofuran (78596-82-4)

Guidance literature:

With dmap; In triethylamine; at 25 ℃; for 24h;

DOI:10.1021/ja00402a039

Reference yield:

1,3-dibenzylphloroglucinol (63604-98-8) → 3-((p-bromobenzenesulfonyl)oxy)-3a-acetoxy-4-(benzyloxy)-6-methoxy-2,3,3a,8a-tetrahydrofuro<2,3-b>benzofuran (78596-82-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 42 percent / HBr / CH₂Cl₂ / 0.33 h / 25 °C

2: 1.) aq. oxalic acid, 2.) aq. sodium hydroxide / 1.) acetone, reflux, 0.5 h, 2.) tetrahydrofuran, 25 deg C, 23.5 h

3: 98 percent / p-toluenesulfonic acid / 3 h / 25 °C

4: 88 percent / hydrogen / 5percent Pd-BaSO₄ / ethyl acetate / 1 h / 25 °C / 760 Torr

5: 98 percent / potassium carbonate / dimethylformamide / 24 h / 25 °C

6: 90 percent / acetic acid / H₂O / 1 h / Heating

7: 95 percent / pyridine / 24 h / 25 °C

8: 100 percent / 4-(N,N-dimethylamino)pyridine / triethylamine / 24 h / 25 °C

With pyridine; dmap; sodium hydroxide; hydrogen bromide; hydrogen; oxalic acid; potassium carbonate; toluene-4-sulfonic acid; acetic acid; palladium on barium sulfate; In dichloromethane; water; ethyl acetate; triethylamine; N,N-dimethyl-formamide;

DOI:10.1021/ja00402a039

Reference yield:

phloroglucinol monobenzenesulfonate (3900-81-0) → 3-((p-bromobenzenesulfonyl)oxy)-3a-acetoxy-4-(benzyloxy)-6-methoxy-2,3,3a,8a-tetrahydrofuro<2,3-b>benzofuran (78596-82-4)

Guidance literature:

Multi-step reaction with 10 steps

1: potassium iodide, potassium carbonate / dimethylformamide / 12 h / 25 °C

2: 95 percent / aq. potassium hydroxide / methanol; H₂O / 18 h / Heating

3: 42 percent / HBr / CH₂Cl₂ / 0.33 h / 25 °C

4: 1.) aq. oxalic acid, 2.) aq. sodium hydroxide / 1.) acetone, reflux, 0.5 h, 2.) tetrahydrofuran, 25 deg C, 23.5 h

5: 98 percent / p-toluenesulfonic acid / 3 h / 25 °C

6: 88 percent / hydrogen / 5percent Pd-BaSO₄ / ethyl acetate / 1 h / 25 °C / 760 Torr

7: 98 percent / potassium carbonate / dimethylformamide / 24 h / 25 °C

8: 90 percent / acetic acid / H₂O / 1 h / Heating

9: 95 percent / pyridine / 24 h / 25 °C

10: 100 percent / 4-(N,N-dimethylamino)pyridine / triethylamine / 24 h / 25 °C

With pyridine; dmap; potassium hydroxide; sodium hydroxide; hydrogen bromide; hydrogen; oxalic acid; potassium carbonate; toluene-4-sulfonic acid; acetic acid; potassium iodide; palladium on barium sulfate; In methanol; dichloromethane; water; ethyl acetate; triethylamine; N,N-dimethyl-formamide;

DOI:10.1021/ja00402a039

upstream raw materials:

acetic anhydride

3-((p-bromobenzenesulfonyl)oxy)-3a-hydroxy-4-(benzyloxy)-6-methoxy-2,3,3a,8a-tetrahydrofuro<2,3-b>benzofuran

1,3-dibenzylphloroglucinol

phloroglucinol monobenzenesulfonate

Downstream raw materials:

3a-acetoxy-4-(benzyloxy)-6-methoxy-3a,8a-dihydrofuro<2,3-b>benzofuran

Refernces