(7E,9E)-(3aR,5R,11R,12R,16R,17S,17aS)-12-Ethyl-2,16-dihydroxy-5,9,17-trimethyl-11-trityloxymethyl-3,3a,4,5,11,12,15,16,17,17a-decahydro-2H-1,13-dioxa-cyclopentacyclohexadecene-6,14-dione

Base Information

• Chemical Name: (7E,9E)-(3aR,5R,11R,12R,16R,17S,17aS)-12-Ethyl-2,16-dihydroxy-5,9,17-trimethyl-11-trityloxymethyl-3,3a,4,5,11,12,15,16,17,17a-decahydro-2H-1,13-dioxa-cyclopentacyclohexadecene-6,14-dione
• CAS No.: 84120-94-5
• Molecular Formula: C₄₂H₅₀O₇
• Molecular Weight: 666.855
• Mol file: 84120-94-5.mol

Synonyms:(7E,9E)-(3aR,5R,11R,12R,16R,17S,17aS)-12-Ethyl-2,16-dihydroxy-5,9,17-trimethyl-11-trityloxymethyl-3,3a,4,5,11,12,15,16,17,17a-decahydro-2H-1,13-dioxa-cyclopentacyclohexadecene-6,14-dione

Chemical Property of (7E,9E)-(3aR,5R,11R,12R,16R,17S,17aS)-12-Ethyl-2,16-dihydroxy-5,9,17-trimethyl-11-trityloxymethyl-3,3a,4,5,11,12,15,16,17,17a-decahydro-2H-1,13-dioxa-cyclopentacyclohexadecene-6,14-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (7E,9E)-(3aR,5R,11R,12R,16R,17S,17aS)-12-Ethyl-2,16-dihydroxy-5,9,17-trimethyl-11-trityloxymethyl-3,3a,4,5,11,12,15,16,17,17a-decahydro-2H-1,13-dioxa-cyclopentacyclohexadecene-6,14-dione

There total 1 articles about (7E,9E)-(3aR,5R,11R,12R,16R,17S,17aS)-12-Ethyl-2,16-dihydroxy-5,9,17-trimethyl-11-trityloxymethyl-3,3a,4,5,11,12,15,16,17,17a-decahydro-2H-1,13-dioxa-cyclopentacyclohexadecene-6,14-dione 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: 78.0%

(7E,9E)-(3aR,5R,11R,12R,16R,17S,17aS)-12-Ethyl-16-hydroxy-2-methoxy-5,9,17-trimethyl-11-trityloxymethyl-3,3a,4,5,11,12,15,16,17,17a-decahydro-2H-1,13-dioxa-cyclopentacyclohexadecene-6,14-dione (81114-52-5,81132-63-0,84171-61-9) → (7E,9E)-(3aR,5R,11R,12R,16R,17S,17aS)-12-Ethyl-2,16-dihydroxy-5,9,17-trimethyl-11-trityloxymethyl-3,3a,4,5,11,12,15,16,17,17a-decahydro-2H-1,13-dioxa-cyclopentacyclohexadecene-6,14-dione (84120-94-5)

Guidance literature:

With phosphoric acid; In tetrahydrofuran; water; at 60 ℃; for 21h;

DOI:10.1016/S0040-4039(00)87619-4

Reference yield: 11.0%

(7E,9E)-(3aR,5R,11R,12R,16R,17S,17aS)-12-Ethyl-2,16-dihydroxy-5,9,17-trimethyl-11-trityloxymethyl-3,3a,4,5,11,12,15,16,17,17a-decahydro-2H-1,13-dioxa-cyclopentacyclohexadecene-6,14-dione (84120-94-5) + ethylene glycol (107-21-1) → (7E,9E)-(3aR,5R,11R,12R,16R,17S,17aS)-12-Ethyl-16-hydroxy-2-(2-hydroxy-ethoxy)-5,9,17-trimethyl-11-trityloxymethyl-3,3a,4,5,11,12,15,16,17,17a-decahydro-2H-1,13-dioxa-cyclopentacyclohexadecene-6,14-dione (84134-60-1) + (11E,13E)-(4R,5S,6S,7R,9R,15R,16R)-7-[1,3]Dioxolan-2-ylmethyl-16-ethyl-4,6-dihydroxy-5,9,13-trimethyl-15-trityloxymethyl-oxacyclohexadeca-11,13-diene-2,10-dione (84130-12-1)

Guidance literature:

toluene-4-sulfonic acid; In 1,4-dioxane; at 35 ℃; for 48h;

DOI:10.1016/S0040-4039(00)87619-4

Reference yield:

(7E,9E)-(3aR,5R,11R,12R,16R,17S,17aS)-12-Ethyl-2,16-dihydroxy-5,9,17-trimethyl-11-trityloxymethyl-3,3a,4,5,11,12,15,16,17,17a-decahydro-2H-1,13-dioxa-cyclopentacyclohexadecene-6,14-dione (84120-94-5) → tylosin (1401-69-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 11 percent / TsOH / dioxane / 48 h / 35 °C

2: 1.) HgO, HgBr₂ / 1.) dioxane, Drierite, 20 deg C, 17 h; 2.) 40 deg C, 24 h

3: 60 percent / acetonitrile / 0.5 h / 5 °C

4: 17 percent / 1,3-dibromo-5,5-dimethylhydantoin / acetonitrile; toluene / 5 h / -30 - 20 °C

5: 82 percent / 90percent CF₃COOH / 1 h / 5 °C

6: 90 percent / Bu3SnH / α,α'-azobisisobutyronitrile / benzene; toluene / 5 h / 45 °C

7: 22 percent / Hg(CN)2 / nitromethane / 6 h / 40 °C

8: MeOH / 48 h / 40 °C

9: 84 percent / K₂CO₃ / methanol / 2 h / 20 °C

With methanol; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; tri-n-butyl-tin hydride; mercury(II) cyanide; potassium carbonate; trifluoroacetic acid; mercury dibromide; mercury(II) oxide; azobisisobutyronitrile; toluene-4-sulfonic acid; In 1,4-dioxane; methanol; nitromethane; toluene; acetonitrile; benzene;

DOI:10.1016/S0040-4039(00)87619-4

upstream raw materials:

(7E,9E)-(3aR,5R,11R,12R,16R,17S,17aS)-12-Ethyl-16-hydroxy-2-methoxy-5,9,17-trimethyl-11-trityloxymethyl-3,3a,4,5,11,12,15,16,17,17a-decahydro-2H-1,13-dioxa-cyclopentacyclohexadecene-6,14-dione

Downstream raw materials:

(7E,9E)-(3aR,5R,11R,12R,16R,17S,17aS)-12-Ethyl-16-hydroxy-2-(2-hydroxy-ethoxy)-5,9,17-trimethyl-11-trityloxymethyl-3,3a,4,5,11,12,15,16,17,17a-decahydro-2H-1,13-dioxa-cyclopentacyclohexadecene-6,14-dione

(11E,13E)-(4R,5S,6S,7R,9R,15R,16R)-7-[1,3]Dioxolan-2-ylmethyl-16-ethyl-4,6-dihydroxy-5,9,13-trimethyl-15-trityloxymethyl-oxacyclohexadeca-11,13-diene-2,10-dione

(11E,13E)-(4R,5S,6S,7R,9R,15R,16R)-6-((2R,3R,4S,5S,6R)-4-Dimethylamino-3,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-7-[1,3]dioxolan-2-ylmethyl-16-ethyl-4-hydroxy-5,9,13-trimethyl-15-trityloxymethyl-oxacyclohexadeca-11,13-diene-2,10-dione

C₅₄H₇₁NO₁₂