2H-1-Benzopyran-2-one, 7-hydroxy-8-[(S)-(4-hydroxy-3,5-dimethoxyphenyl)-(2R)-oxiranylmethoxy ]-

Base Information

• Chemical Name: 2H-1-Benzopyran-2-one, 7-hydroxy-8-[(S)-(4-hydroxy-3,5-dimethoxyphenyl)-(2R)-oxiranylmethoxy ]-
• CAS No.: 477770-86-8
• Molecular Formula: C20H18O8
• Molecular Weight: 386.358
• Mol file: 477770-86-8.mol

Synonyms:

Chemical Property of 2H-1-Benzopyran-2-one, 7-hydroxy-8-[(S)-(4-hydroxy-3,5-dimethoxyphenyl)-(2R)-oxiranylmethoxy ]-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2H-1-Benzopyran-2-one, 7-hydroxy-8-[(S)-(4-hydroxy-3,5-dimethoxyphenyl)-(2R)-oxiranylmethoxy ]-

There total 12 articles about 2H-1-Benzopyran-2-one, 7-hydroxy-8-[(S)-(4-hydroxy-3,5-dimethoxyphenyl)-(2R)-oxiranylmethoxy ]- 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: 75.0%

(1S,2R)-7-benzyloxy-8-[2,3-epoxy-1-(4-benzyloxy-3,5-dimethoxyphenyl)propoxy]coumarin (477770-85-7) → (1S,2R)-7-hydroxy-8-[2,3-epoxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propoxy]coumarin (477770-86-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; at 20 ℃; for 6h;

DOI:10.1016/S0957-4166(02)00482-2

Reference yield:

7-hydroxy-2H-chromen-2-one (93-35-6) → (1S,2R)-7-hydroxy-8-[2,3-epoxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propoxy]coumarin (477770-86-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 97 percent / pyridine / CH₂Cl₂ / 24 h / 20 °C

2.1: 79 percent / AlCl₃ / 2 h / 160 °C

3.1: 94 percent / K₂CO₃ / acetone / 24 h / 20 °C

4.1: 94 percent / aq. H₂O₂; aq. NaOH / dioxane / 0.33 h / 10 °C

5.1: K₂CO₃ / methanol / 3 h / 20 °C

5.2: PPh₃; DIAD / tetrahydrofuran / 24 h / 20 °C

6.1: 75 percent / H₂ / 5 percent Pd/C / ethyl acetate / 6 h / 20 °C

With pyridine; sodium hydroxide; aluminium trichloride; hydrogen; dihydrogen peroxide; potassium carbonate; palladium on activated charcoal; In 1,4-dioxane; methanol; dichloromethane; ethyl acetate; acetone; 4.1: Baeyer-Villiger oxidation / 5.2: Mitsunobu reaction;

DOI:10.1016/S0957-4166(02)00482-2

Reference yield:

7-acetyloxycoumarin (10387-49-2) → (1S,2R)-7-hydroxy-8-[2,3-epoxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propoxy]coumarin (477770-86-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 79 percent / AlCl₃ / 2 h / 160 °C

2.1: 94 percent / K₂CO₃ / acetone / 24 h / 20 °C

3.1: 94 percent / aq. H₂O₂; aq. NaOH / dioxane / 0.33 h / 10 °C

4.1: K₂CO₃ / methanol / 3 h / 20 °C

4.2: PPh₃; DIAD / tetrahydrofuran / 24 h / 20 °C

5.1: 75 percent / H₂ / 5 percent Pd/C / ethyl acetate / 6 h / 20 °C

With sodium hydroxide; aluminium trichloride; hydrogen; dihydrogen peroxide; potassium carbonate; palladium on activated charcoal; In 1,4-dioxane; methanol; ethyl acetate; acetone; 3.1: Baeyer-Villiger oxidation / 4.2: Mitsunobu reaction;

DOI:10.1016/S0957-4166(02)00482-2

upstream raw materials:

(1S,2R)-7-benzyloxy-8-[2,3-epoxy-1-(4-benzyloxy-3,5-dimethoxyphenyl)propoxy]coumarin

7-hydroxy-2H-chromen-2-one

7-acetyloxycoumarin

8-acetyl-7-hydroxycoumarin

Downstream raw materials:

daphneticin