(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

Base Information

Chemical Name:(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
CAS No.:84130-12-1
Molecular Formula:C₄₄H₅₄O₈
Molecular Weight:710.908
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 2 articles about (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 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: 11.0%

: 84120-94-5
(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

: 107-21-1
ethylene glycol

: 84134-60-1
(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

: 84130-12-1
(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

Guidance literature:: toluene-4-sulfonic acid; In 1,4-dioxane; at 35 ℃; for 48h;
DOI:10.1016/S0040-4039(00)87619-4

Reference yield:

: 81114-52-5,81132-63-0,84171-61-9
(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

: 84130-12-1
(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

Guidance literature:: Multi-step reaction with 2 steps

1: 78 percent / H₃PO₄ / tetrahydrofuran; H₂O / 21 h / 60 °C

2: 11 percent / TsOH / dioxane / 48 h / 35 °C

With phosphoric acid; toluene-4-sulfonic acid; In tetrahydrofuran; 1,4-dioxane; water;
DOI:10.1016/S0040-4039(00)87619-4

Reference yield:

: 84130-12-1
(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

: 1401-69-0
tylosin

Guidance literature:: Multi-step reaction with 8 steps

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

2: 60 percent / acetonitrile / 0.5 h / 5 °C

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

4: 82 percent / 90percent CF₃COOH / 1 h / 5 °C

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

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

7: MeOH / 48 h / 40 °C

8: 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; In methanol; nitromethane; toluene; acetonitrile; benzene;
DOI:10.1016/S0040-4039(00)87619-4