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

Base Information

• Chemical Name: 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
• CAS No.: 325781-14-4
• Molecular Formula: C₄₇H₅₄O₈
• Molecular Weight: 746.941
• Mol file: 325781-14-4.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 10 articles about 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 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: 27.0%

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 (325781-13-3) → 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 (325781-14-4)

Guidance literature:

With sodium acetate; pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1271/bbb.64.2429

Reference yield:

phorbol (17673-25-5) → 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 (325781-14-4)

Guidance literature:

Multi-step reaction with 9 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

4: 86 percent / NaBH₄; CeCl₃*7H₂O / CH₂Cl₂; methanol / 0.67 h / -78 °C

5: 49 percent / NaBH₄; CeCl₃*7H₂O / methanol / 0.33 h / 20 °C

6: 100 percent / H₃BO₃ / acetonitrile / 0.25 h / 20 °C

7: 4-dimethylaminopyridine; Et₃N / CH₂Cl₂ / 2 h / 20 °C

8: 8.4 mg / water / CH₂Cl₂; CHCl₃ / 0.33 h

9: 27 percent / pyridinium chlorochromate; sodium acetate / CH₂Cl₂ / 0.5 h / 20 °C

With pyridine; dmap; sodium tetrahydroborate; cerium(III) chloride; water; sodium acetate; boric acid; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane; chloroform; acetonitrile;

DOI:10.1271/bbb.64.2429

Reference yield:

phorbol-20-trityl ether (82400-03-1) → 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 (325781-14-4)

Guidance literature:

Multi-step reaction with 8 steps

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

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

3: 86 percent / NaBH₄; CeCl₃*7H₂O / CH₂Cl₂; methanol / 0.67 h / -78 °C

4: 49 percent / NaBH₄; CeCl₃*7H₂O / methanol / 0.33 h / 20 °C

5: 100 percent / H₃BO₃ / acetonitrile / 0.25 h / 20 °C

6: 4-dimethylaminopyridine; Et₃N / CH₂Cl₂ / 2 h / 20 °C

7: 8.4 mg / water / CH₂Cl₂; CHCl₃ / 0.33 h

8: 27 percent / pyridinium chlorochromate; sodium acetate / CH₂Cl₂ / 0.5 h / 20 °C

With dmap; sodium tetrahydroborate; cerium(III) chloride; water; sodium acetate; boric acid; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane; chloroform; acetonitrile;

DOI:10.1271/bbb.64.2429

upstream raw materials:

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

phorbol

phorbol-20-trityl ether

trityl chloride

Downstream raw materials:

12-epi-phorbol-12,13-dibutyrate

Refernces