Phenyl-acetic acid (1aR,1bS,4aR,7aS,7bR,8S,9aS)-4a,7b-dihydroxy-3-{2-[3-methoxy-4-(2-methoxy-ethoxymethoxy)-phenyl]-acetoxymethyl}-1,1,6,8-tetramethyl-5,9-dioxo-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl ester

Base Information

• Chemical Name: Phenyl-acetic acid (1aR,1bS,4aR,7aS,7bR,8S,9aS)-4a,7b-dihydroxy-3-{2-[3-methoxy-4-(2-methoxy-ethoxymethoxy)-phenyl]-acetoxymethyl}-1,1,6,8-tetramethyl-5,9-dioxo-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl ester
• CAS No.: 1025934-50-2
• Molecular Formula: C₄₁H₄₈O₁₂
• Molecular Weight: 732.825

Synonyms:Phenyl-acetic acid (1aR,1bS,4aR,7aS,7bR,8S,9aS)-4a,7b-dihydroxy-3-{2-[3-methoxy-4-(2-methoxy-ethoxymethoxy)-phenyl]-acetoxymethyl}-1,1,6,8-tetramethyl-5,9-dioxo-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl ester

Chemical Property of Phenyl-acetic acid (1aR,1bS,4aR,7aS,7bR,8S,9aS)-4a,7b-dihydroxy-3-{2-[3-methoxy-4-(2-methoxy-ethoxymethoxy)-phenyl]-acetoxymethyl}-1,1,6,8-tetramethyl-5,9-dioxo-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl ester

Chemical Property:

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Technology Process of Phenyl-acetic acid (1aR,1bS,4aR,7aS,7bR,8S,9aS)-4a,7b-dihydroxy-3-{2-[3-methoxy-4-(2-methoxy-ethoxymethoxy)-phenyl]-acetoxymethyl}-1,1,6,8-tetramethyl-5,9-dioxo-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl ester

There total 7 articles about Phenyl-acetic acid (1aR,1bS,4aR,7aS,7bR,8S,9aS)-4a,7b-dihydroxy-3-{2-[3-methoxy-4-(2-methoxy-ethoxymethoxy)-phenyl]-acetoxymethyl}-1,1,6,8-tetramethyl-5,9-dioxo-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl 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: 75.0%

MEM-homovanillic acid (179258-48-1) + Phenyl-acetic acid (1aR,1bS,4aR,7aS,7bR,8S,9aS)-4a,7b-dihydroxy-3-hydroxymethyl-1,1,6,8-tetramethyl-5,9-dioxo-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl ester (179258-45-8) → Phenyl-acetic acid (1aR,1bS,4aR,7aS,7bR,8S,9aS)-4a,7b-dihydroxy-3-{2-[3-methoxy-4-(2-methoxy-ethoxymethoxy)-phenyl]-acetoxymethyl}-1,1,6,8-tetramethyl-5,9-dioxo-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl ester (1025934-50-2)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1021/jm960063l

Reference yield:

phenylacetic acid (103-82-2) → Phenyl-acetic acid (1aR,1bS,4aR,7aS,7bR,8S,9aS)-4a,7b-dihydroxy-3-{2-[3-methoxy-4-(2-methoxy-ethoxymethoxy)-phenyl]-acetoxymethyl}-1,1,6,8-tetramethyl-5,9-dioxo-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl ester (1025934-50-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 33 percent / dicyclohexylcarbodiimide, 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.5 h / Ambient temperature

2: pyridinium chlorochromate, molecular sieves 4 Angstroem / CH₂Cl₂ / 3 h / Ambient temperature

3: HClO₄ / methanol / 0.83 h / Ambient temperature

4: 75 percent / dicyclohexylcarbodiimide, 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h / Ambient temperature

With dmap; perchloric acid; 4 A molecular sieve; dicyclohexyl-carbodiimide; pyridinium chlorochromate; In methanol; dichloromethane;

DOI:10.1021/jm960063l

Reference yield:

4-hydroxy-3-methoxyphenylacetonitrile (4468-59-1) → Phenyl-acetic acid (1aR,1bS,4aR,7aS,7bR,8S,9aS)-4a,7b-dihydroxy-3-{2-[3-methoxy-4-(2-methoxy-ethoxymethoxy)-phenyl]-acetoxymethyl}-1,1,6,8-tetramethyl-5,9-dioxo-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl ester (1025934-50-2)

Guidance literature:

Multi-step reaction with 3 steps

1: N-ethyldiisopropylamine / CH₂Cl₂ / 48 h / Ambient temperature

2: 6.6 aq. N KOH / ethanol / 12 h / Heating

3: 75 percent / dicyclohexylcarbodiimide, 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h / Ambient temperature

With dmap; potassium hydroxide; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In ethanol; dichloromethane;

DOI:10.1021/jm960063l

upstream raw materials:

MEM-homovanillic acid

Phenyl-acetic acid (1aR,1bS,4aR,7aS,7bR,8S,9aS)-4a,7b-dihydroxy-3-hydroxymethyl-1,1,6,8-tetramethyl-5,9-dioxo-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl ester

phenylacetic acid

4-hydroxy-3-methoxyphenylacetonitrile

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