Butyric acid (1aR,1bS,4aR,7aS,7bR,8S,9aS)-4a,7b-dihydroxy-1,1,6,8-tetramethyl-5,9-dioxo-3-trityloxymethyl-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: Butyric acid (1aR,1bS,4aR,7aS,7bR,8S,9aS)-4a,7b-dihydroxy-1,1,6,8-tetramethyl-5,9-dioxo-3-trityloxymethyl-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl ester
• CAS No.: 325781-10-0
• Molecular Formula: C₄₃H₄₆O₇
• Molecular Weight: 674.834

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

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

There total 4 articles about Butyric acid (1aR,1bS,4aR,7aS,7bR,8S,9aS)-4a,7b-dihydroxy-1,1,6,8-tetramethyl-5,9-dioxo-3-trityloxymethyl-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: 60.0%

Butyric acid (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-4a,7b,9-trihydroxy-1,1,6,8-tetramethyl-5-oxo-3-trityloxymethyl-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl ester (325781-09-7) → Butyric acid (1aR,1bS,4aR,7aS,7bR,8S,9aS)-4a,7b-dihydroxy-1,1,6,8-tetramethyl-5,9-dioxo-3-trityloxymethyl-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl ester (325781-10-0)

Guidance literature:

With sodium acetate; pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1271/bbb.64.2429

Reference yield:

phorbol (17673-25-5) → Butyric acid (1aR,1bS,4aR,7aS,7bR,8S,9aS)-4a,7b-dihydroxy-1,1,6,8-tetramethyl-5,9-dioxo-3-trityloxymethyl-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl ester (325781-10-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 63 percent / pyridine

2: 78 percent / triethzlamine / CH₂Cl₂; tetrahydrofuran / 9 h / 20 °C

3: 60 percent / pyridinium chlorochromate; sodium acetate / CH₂Cl₂ / 3 h / 20 °C

With pyridine; sodium acetate; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane;

DOI:10.1271/bbb.64.2429

Reference yield:

phorbol-20-trityl ether (82400-03-1) → Butyric acid (1aR,1bS,4aR,7aS,7bR,8S,9aS)-4a,7b-dihydroxy-1,1,6,8-tetramethyl-5,9-dioxo-3-trityloxymethyl-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl ester (325781-10-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / triethzlamine / CH₂Cl₂; tetrahydrofuran / 9 h / 20 °C

2: 60 percent / pyridinium chlorochromate; sodium acetate / CH₂Cl₂ / 3 h / 20 °C

With sodium acetate; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane;

DOI:10.1271/bbb.64.2429

upstream raw materials:

Butyric acid (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-4a,7b,9-trihydroxy-1,1,6,8-tetramethyl-5-oxo-3-trityloxymethyl-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl ester

phorbol

phorbol-20-trityl ether

trityl chloride

Downstream raw materials:

Butyric acid (1aR,1bS,4aR,5S,7aS,7bR,8S,9aS)-4a,5,7b-trihydroxy-1,1,6,8-tetramethyl-9-oxo-3-trityloxymethyl-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl ester

Butyric acid (1aR,1bS,4aR,5S,7aS,7bS,8R,9S,9aS)-9-butyryloxy-4a,5,7b-trihydroxy-1,1,6,8-tetramethyl-3-trityloxymethyl-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl ester

Butyric acid (1aR,1bS,4aR,7aS,7bS,8R,9S,9aS)-9-butyryloxy-4a,7b-dihydroxy-1,1,6,8-tetramethyl-5-oxo-3-trityloxymethyl-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl ester

Butyric acid (1aR,1bS,4aR,5S,7aS,7bS,8R,9S,9aS)-4a,5,7b,9-tetrahydroxy-1,1,6,8-tetramethyl-3-trityloxymethyl-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl ester

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