2-(4-benzyloxy-3-methoxy-2-methoxycarbonylphenyl)-6,7-methylenedioxy-1-(N-methylformamido)naphthalene

Base Information

• Chemical Name: 2-(4-benzyloxy-3-methoxy-2-methoxycarbonylphenyl)-6,7-methylenedioxy-1-(N-methylformamido)naphthalene
• CAS No.: 171078-14-1
• Molecular Formula: C₂₉H₂₅NO₇
• Molecular Weight: 499.52

Synonyms:2-(4-benzyloxy-3-methoxy-2-methoxycarbonylphenyl)-6,7-methylenedioxy-1-(N-methylformamido)naphthalene

Chemical Property of 2-(4-benzyloxy-3-methoxy-2-methoxycarbonylphenyl)-6,7-methylenedioxy-1-(N-methylformamido)naphthalene

Chemical Property:

Purity/Quality:

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Technology Process of 2-(4-benzyloxy-3-methoxy-2-methoxycarbonylphenyl)-6,7-methylenedioxy-1-(N-methylformamido)naphthalene

There total 8 articles about 2-(4-benzyloxy-3-methoxy-2-methoxycarbonylphenyl)-6,7-methylenedioxy-1-(N-methylformamido)naphthalene 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%

dimethyl sulfate (77-78-1) + 3-Benzyloxy-6-[5-(formyl-methyl-amino)-naphtho[2,3-d][1,3]dioxol-6-yl]-2-methoxy-benzoic acid (1027165-78-1) → 2-(4-benzyloxy-3-methoxy-2-methoxycarbonylphenyl)-6,7-methylenedioxy-1-(N-methylformamido)naphthalene (171078-14-1)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; for 0.166667h; Ambient temperature;

DOI:10.1248/cpb.43.766

Reference yield:

2-<4-(7-methoxy-2-methyl-2H-benzofuranyl)>-1-(N-methylformamido)-6,7-methylenedioxynaphthalene (130627-27-9) → 2-(4-benzyloxy-3-methoxy-2-methoxycarbonylphenyl)-6,7-methylenedioxy-1-(N-methylformamido)naphthalene (171078-14-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 49 percent / trimethylsilyl iodide / quinoline / 2 h / 180 °C

2: K₂CO₃ / dimethylformamide / 2 h / 60 °C

3: 1.) osmium tetroxide, 2.) sodium hydrogen sulfite / 1.) pyridine, RT, 3 h, 2.) pyridine, water, RT, 3 h

4: periodic acid / dioxane; H₂O / 1.5 h / Ambient temperature

5: 5percent aq. NaOH / dioxane / 0.08 h / Ambient temperature

6: 95 percent / benzyltributylammonium chloride, sodium hydroxide / CH₂Cl₂; H₂O / 0.25 h / Ambient temperature

7: 0.072 g / aq. sodium phosphate monobasic dihydrate, 30percent aq. hydrogen peroxide, aq. sodium chlorite / acetonitrile / 4 h / 10 °C

8: 92 percent / K₂CO₃ / dimethylformamide / 0.17 h / Ambient temperature

With sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; osmium(VIII) oxide; trimethylsilyl iodide; dihydrogen peroxide; benzyltri(n-butyl)ammonium chloride; potassium carbonate; sodium hydrogensulfite; periodic acid; In 1,4-dioxane; quinoline; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1248/cpb.43.766

Reference yield:

2-<4-(7-hydroxy-2-methylbenzofuranyl)>-6,7-methylenedioxy-1-(N-methylformamido)naphthalene (171078-08-3) → 2-(4-benzyloxy-3-methoxy-2-methoxycarbonylphenyl)-6,7-methylenedioxy-1-(N-methylformamido)naphthalene (171078-14-1)

Guidance literature:

Multi-step reaction with 7 steps

1: K₂CO₃ / dimethylformamide / 2 h / 60 °C

2: 1.) osmium tetroxide, 2.) sodium hydrogen sulfite / 1.) pyridine, RT, 3 h, 2.) pyridine, water, RT, 3 h

3: periodic acid / dioxane; H₂O / 1.5 h / Ambient temperature

4: 5percent aq. NaOH / dioxane / 0.08 h / Ambient temperature

5: 95 percent / benzyltributylammonium chloride, sodium hydroxide / CH₂Cl₂; H₂O / 0.25 h / Ambient temperature

6: 0.072 g / aq. sodium phosphate monobasic dihydrate, 30percent aq. hydrogen peroxide, aq. sodium chlorite / acetonitrile / 4 h / 10 °C

7: 92 percent / K₂CO₃ / dimethylformamide / 0.17 h / Ambient temperature

With sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; osmium(VIII) oxide; dihydrogen peroxide; benzyltri(n-butyl)ammonium chloride; potassium carbonate; sodium hydrogensulfite; periodic acid; In 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1248/cpb.43.766

upstream raw materials:

dimethyl sulfate

3-Benzyloxy-6-[5-(formyl-methyl-amino)-naphtho[2,3-d][1,3]dioxol-6-yl]-2-methoxy-benzoic acid

2-<4-(7-methoxy-2-methyl-2H-benzofuranyl)>-1-(N-methylformamido)-6,7-methylenedioxynaphthalene

2-<4-(7-hydroxy-2-methylbenzofuranyl)>-6,7-methylenedioxy-1-(N-methylformamido)naphthalene

Downstream raw materials:

8-benzyloxy-7-methoxy-5-methyl-2,3-methylenedioxybenzophenanthridin-6(5H)-one

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