(11E,16E)-(2R,5R,10S,15S,18S)-10-Ethyl-18-methoxy-11,15-dimethyl-13-methylene-2-(2,4,6-trimethyl-phenyl)-1,3,9-trioxa-spiro[4.13]octadeca-11,16-diene-6,8-dione

Base Information

• Chemical Name: (11E,16E)-(2R,5R,10S,15S,18S)-10-Ethyl-18-methoxy-11,15-dimethyl-13-methylene-2-(2,4,6-trimethyl-phenyl)-1,3,9-trioxa-spiro[4.13]octadeca-11,16-diene-6,8-dione
• CAS No.: 594854-78-1
• Molecular Formula: C₃₀H₄₀O₆
• Molecular Weight: 496.644
• Mol file: 594854-78-1.mol

Synonyms:

Chemical Property of (11E,16E)-(2R,5R,10S,15S,18S)-10-Ethyl-18-methoxy-11,15-dimethyl-13-methylene-2-(2,4,6-trimethyl-phenyl)-1,3,9-trioxa-spiro[4.13]octadeca-11,16-diene-6,8-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (11E,16E)-(2R,5R,10S,15S,18S)-10-Ethyl-18-methoxy-11,15-dimethyl-13-methylene-2-(2,4,6-trimethyl-phenyl)-1,3,9-trioxa-spiro[4.13]octadeca-11,16-diene-6,8-dione

There total 6 articles about (11E,16E)-(2R,5R,10S,15S,18S)-10-Ethyl-18-methoxy-11,15-dimethyl-13-methylene-2-(2,4,6-trimethyl-phenyl)-1,3,9-trioxa-spiro[4.13]octadeca-11,16-diene-6,8-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:

(2R,4R)-4-((2E,7E)-(1S,4S,9S)-9-Acetoxy-1-methoxy-4,8-dimethyl-6-methylene-undeca-2,7-dienyl)-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxolane-4-carboxylic acid methyl ester (594854-76-9) → (11E,16E)-(2R,5R,10S,15S,18S)-10-Ethyl-18-methoxy-11,15-dimethyl-13-methylene-2-(2,4,6-trimethyl-phenyl)-1,3,9-trioxa-spiro[4.13]octadeca-11,16-diene-6,8-dione (594854-78-1)

Guidance literature:

With lithium hexamethyldisilazane; In N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1016/j.bmcl.2003.09.072

Reference yield:

(2E,7E)-(4S,9S)-4,8-Dimethyl-6-methylene-9-(2-trimethylsilanyl-ethoxymethoxy)-undeca-2,7-dienal (594854-65-6) → (11E,16E)-(2R,5R,10S,15S,18S)-10-Ethyl-18-methoxy-11,15-dimethyl-13-methylene-2-(2,4,6-trimethyl-phenyl)-1,3,9-trioxa-spiro[4.13]octadeca-11,16-diene-6,8-dione (594854-78-1)

Guidance literature:

Multi-step reaction with 6 steps

1: LHMDS / hexamethylphosphoric acid triamide

2: potassium hexamethyldisilazane

3: tetraethylammonium fluoride

4: DMAP; pyridine

5: LHMDS / hexamethylphosphoric acid triamide

With pyridine; dmap; potassium hexamethyldisilazane; tetraethylammonium fluoride; lithium hexamethyldisilazane; In N,N,N,N,N,N-hexamethylphosphoric triamide; 6: Macro-Dieckmann cyclization;

DOI:10.1016/j.bmcl.2003.09.072

Reference yield:

(2E,7E)-(4S,9S)-4,8-Dimethyl-6-methylene-9-(2-trimethylsilanyl-ethoxymethoxy)-undeca-2,7-dien-1-ol (594854-64-5) → (11E,16E)-(2R,5R,10S,15S,18S)-10-Ethyl-18-methoxy-11,15-dimethyl-13-methylene-2-(2,4,6-trimethyl-phenyl)-1,3,9-trioxa-spiro[4.13]octadeca-11,16-diene-6,8-dione (594854-78-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 82 percent / tetrapropylammonium perruthenate; NMO; MS₄A

2: LHMDS / hexamethylphosphoric acid triamide

3: potassium hexamethyldisilazane

4: tetraethylammonium fluoride

5: DMAP; pyridine

6: LHMDS / hexamethylphosphoric acid triamide

With pyridine; dmap; N-methyl-2-indolinone; tetrapropylammonium perruthennate; potassium hexamethyldisilazane; tetraethylammonium fluoride; lithium hexamethyldisilazane; In N,N,N,N,N,N-hexamethylphosphoric triamide; 7: Macro-Dieckmann cyclization;

DOI:10.1016/j.bmcl.2003.09.072

upstream raw materials:

(2R,4R)-4-((2E,7E)-(1S,4S,9S)-9-Acetoxy-1-methoxy-4,8-dimethyl-6-methylene-undeca-2,7-dienyl)-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxolane-4-carboxylic acid methyl ester

(2E,7E)-(4S,9S)-4,8-Dimethyl-6-methylene-9-(2-trimethylsilanyl-ethoxymethoxy)-undeca-2,7-dienal

(2E,7E)-(4S,9S)-4,8-Dimethyl-6-methylene-9-(2-trimethylsilanyl-ethoxymethoxy)-undeca-2,7-dien-1-ol

(2E,7E)-(4S,9S)-4,8-Dimethyl-6-methylene-9-(2-trimethylsilanyl-ethoxymethoxy)-undeca-2,7-dienoic acid ethyl ester

Downstream raw materials:

(11E,16E)-(2R,5R,7R,10S,15S,18S)-10-Ethyl-18-methoxy-7,11,15-trimethyl-13-methylene-2-(2,4,6-trimethyl-phenyl)-1,3,9-trioxa-spiro[4.13]octadeca-11,16-diene-6,8-dione