Carbonic acid (6R,7R,8R)-6-ethoxycarbonyloxymethyl-8-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]quinolin-7-ylmethyl ester ethyl ester

Base Information

• Chemical Name: Carbonic acid (6R,7R,8R)-6-ethoxycarbonyloxymethyl-8-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]quinolin-7-ylmethyl ester ethyl ester
• CAS No.: 256331-37-0
• Molecular Formula: C₂₇H₃₃NO₁₁
• Molecular Weight: 547.559

Synonyms:Carbonic acid (6R,7R,8R)-6-ethoxycarbonyloxymethyl-8-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]quinolin-7-ylmethyl ester ethyl ester

Chemical Property of Carbonic acid (6R,7R,8R)-6-ethoxycarbonyloxymethyl-8-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]quinolin-7-ylmethyl ester ethyl ester

Chemical Property:

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Technology Process of Carbonic acid (6R,7R,8R)-6-ethoxycarbonyloxymethyl-8-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]quinolin-7-ylmethyl ester ethyl ester

There total 13 articles about Carbonic acid (6R,7R,8R)-6-ethoxycarbonyloxymethyl-8-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]quinolin-7-ylmethyl ester ethyl 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: 60.0%

6-[(1R,2S,3S)-4-Ethoxycarbonyloxy-2-ethoxycarbonyloxymethyl-3-methanesulfonyloxy-1-(3,4,5-trimethoxy-phenyl)-butyl]-benzo[1,3]dioxole-5-carboxylic acid (256331-34-7) → Carbonic acid (6R,7R,8R)-6-ethoxycarbonyloxymethyl-8-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]quinolin-7-ylmethyl ester ethyl ester (256331-37-0) + Carbonic acid (2S,3S,4R)-3-ethoxycarbonyloxymethyl-4-(6-formyl-benzo[1,3]dioxol-5-yl)-2-iodo-4-(3,4,5-trimethoxy-phenyl)-butyl ester ethyl ester (256331-36-9)

Guidance literature:

With diphenyl-phosphinic acid; triethylamine; In 1,4-dioxane; at 20 - 120 ℃;

DOI:10.1016/S0040-4039(99)01932-2

Reference yield:

Carbonic acid (2S,3S,4R)-3-ethoxycarbonyloxymethyl-4-(6-formyl-benzo[1,3]dioxol-5-yl)-2-iodo-4-(3,4,5-trimethoxy-phenyl)-butyl ester ethyl ester (256331-36-9) → Carbonic acid (6R,7R,8R)-6-ethoxycarbonyloxymethyl-8-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]quinolin-7-ylmethyl ester ethyl ester (256331-37-0)

Guidance literature:

Carbonic acid (2S,3S,4R)-3-ethoxycarbonyloxymethyl-4-(6-formyl-benzo[1,3]dioxol-5-yl)-2-iodo-4-(3,4,5-trimethoxy-phenyl)-butyl ester ethyl ester; With sodium chlorite; 2-methyl-but-2-ene; In tert-butyl alcohol; pH=4;

With 1H-imidazole; iodine; triphenylphosphine; In toluene; at 90 ℃;

DOI:10.1016/S0040-4039(99)01932-2

Reference yield:

Carbonic acid (5R,6R)-7-ethoxycarbonyloxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6-dihydro-naphtho[2,3-d][1,3]dioxol-6-ylmethyl ester ethyl ester → Carbonic acid (6R,7R,8R)-6-ethoxycarbonyloxymethyl-8-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]quinolin-7-ylmethyl ester ethyl ester (256331-37-0)

Guidance literature:

Multi-step reaction with 6 steps

1: O₃; Me₂S / methanol; CHCl₃ / -78 °C

2: 24 percent / BH₃ / tetrahydrofuran / 20 °C

3: 84 percent / MnO₂ / acetonitrile / 20 °C

4: 84 percent / Et₃N / methanol / 20 °C

5: 100 percent / NaClO₂; 2-methyl-2-butene / 2-methyl-propan-2-ol / pH 4

6: 60 percent / DPPA; Et₃N / dioxane / 20 - 120 °C

With manganese(IV) oxide; sodium chlorite; 2-methyl-but-2-ene; dimethylsulfide; diphenyl-phosphinic acid; borane; ozone; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; chloroform; acetonitrile; tert-butyl alcohol; 1: Oxidation / 2: Reduction / 3: Oxidation / 4: Esterification / 5: Oxidation / 6: Substitution;

DOI:10.1016/S0040-4039(99)01932-2

upstream raw materials:

6-[(1R,2S,3S)-4-Ethoxycarbonyloxy-2-ethoxycarbonyloxymethyl-3-methanesulfonyloxy-1-(3,4,5-trimethoxy-phenyl)-butyl]-benzo[1,3]dioxole-5-carboxylic acid

Carbonic acid (2S,3S,4R)-3-ethoxycarbonyloxymethyl-4-(6-formyl-benzo[1,3]dioxol-5-yl)-2-iodo-4-(3,4,5-trimethoxy-phenyl)-butyl ester ethyl ester

Carbonic acid (3S,4R)-3-ethoxycarbonyloxymethyl-4-(6-formyl-benzo[1,3]dioxol-5-yl)-2-oxo-4-(3,4,5-trimethoxy-phenyl)-butyl ester ethyl ester

Carbonic acid (2S,3S,4R)-3-ethoxycarbonyloxymethyl-4-(6-formyl-benzo[1,3]dioxol-5-yl)-2-hydroxy-4-(3,4,5-trimethoxy-phenyl)-butyl ester ethyl ester

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