(E)-(1S,2R,5R,11R,13R)-5-((1E,3E)-4-Bromo-buta-1,3-dienyl)-13-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-2,7,10,10-tetramethyl-4,15-dioxa-bicyclo[9.3.1]pentadec-7-ene-3,9-dione

Base Information

• Chemical Name: (E)-(1S,2R,5R,11R,13R)-5-((1E,3E)-4-Bromo-buta-1,3-dienyl)-13-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-2,7,10,10-tetramethyl-4,15-dioxa-bicyclo[9.3.1]pentadec-7-ene-3,9-dione
• CAS No.: 909016-51-9
• Molecular Formula: C₃₇H₄₇BrO₆Si
• Molecular Weight: 695.766

Synonyms:(E)-(1S,2R,5R,11R,13R)-5-((1E,3E)-4-Bromo-buta-1,3-dienyl)-13-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-2,7,10,10-tetramethyl-4,15-dioxa-bicyclo[9.3.1]pentadec-7-ene-3,9-dione

Chemical Property of (E)-(1S,2R,5R,11R,13R)-5-((1E,3E)-4-Bromo-buta-1,3-dienyl)-13-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-2,7,10,10-tetramethyl-4,15-dioxa-bicyclo[9.3.1]pentadec-7-ene-3,9-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(1S,2R,5R,11R,13R)-5-((1E,3E)-4-Bromo-buta-1,3-dienyl)-13-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-2,7,10,10-tetramethyl-4,15-dioxa-bicyclo[9.3.1]pentadec-7-ene-3,9-dione

There total 6 articles about (E)-(1S,2R,5R,11R,13R)-5-((1E,3E)-4-Bromo-buta-1,3-dienyl)-13-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-2,7,10,10-tetramethyl-4,15-dioxa-bicyclo[9.3.1]pentadec-7-ene-3,9-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: 27.0%

(E)-(1S,5R,11R,13R)-5-((1E,3E)-4-Bromo-buta-1,3-dienyl)-13-(tert-butyl-diphenyl-silanyloxy)-1,9-dihydroxy-2,7,10,10-tetramethyl-4,15-dioxa-bicyclo[9.3.1]pentadec-7-en-3-one → (E)-(1S,2R,5R,11R,13R)-5-((1E,3E)-4-Bromo-buta-1,3-dienyl)-13-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-2,7,10,10-tetramethyl-4,15-dioxa-bicyclo[9.3.1]pentadec-7-ene-3,9-dione (909016-51-9) + (E)-(1S,5R,11R,13R)-5-((1E,3Z)-4-Bromo-buta-1,3-dienyl)-13-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-2,7,10,10-tetramethyl-4,15-dioxa-bicyclo[9.3.1]pentadec-7-ene-3,9-dione + (E)-(1S,2S,5R,11R,13R)-5-((1E,3E)-4-Bromo-buta-1,3-dienyl)-13-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-2,7,10,10-tetramethyl-4,15-dioxa-bicyclo[9.3.1]pentadec-7-ene-3,9-dione (909016-48-4)

Guidance literature:

With pyridine; Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/j.tet.2006.05.077

Reference yield:

(E)-(1S,5R,11R,13R)-5-((1E,3E)-4-Bromo-buta-1,3-dienyl)-13-(tert-butyl-diphenyl-silanyloxy)-9-hydroxy-1-methoxy-2,7,10,10-tetramethyl-4,15-dioxa-bicyclo[9.3.1]pentadec-7-en-3-one → (E)-(1S,2R,5R,11R,13R)-5-((1E,3E)-4-Bromo-buta-1,3-dienyl)-13-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-2,7,10,10-tetramethyl-4,15-dioxa-bicyclo[9.3.1]pentadec-7-ene-3,9-dione (909016-51-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / aq. AcOH / acetone / 0.5 h / 20 °C

2: 27 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C

With pyridine; Dess-Martin periodane; acetic acid; In dichloromethane; acetone; 2: Dess-Martin oxidation;

DOI:10.1016/j.tet.2006.05.077

Reference yield:

2-[(2S,4R,6R)-6-((3E,7E,9E)-(R)-10-Bromo-2,6-dihydroxy-1,1,4-trimethyl-deca-3,7,9-trienyl)-4-(tert-butyl-diphenyl-silanyloxy)-2-methoxy-tetrahydro-pyran-2-yl]-propionic acid methyl ester → (E)-(1S,2R,5R,11R,13R)-5-((1E,3E)-4-Bromo-buta-1,3-dienyl)-13-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-2,7,10,10-tetramethyl-4,15-dioxa-bicyclo[9.3.1]pentadec-7-ene-3,9-dione (909016-51-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 63 percent / aq. NaOH / methanol; tetrahydrofuran / 23 h / 40 °C

2: Et₃N / tetrahydrofuran / 2 h / 20 °C

3: 8.5 mg / Et₃N; DMAP / tetrahydrofuran; toluene / 0.5 h / Heating

4: 86 percent / aq. AcOH / acetone / 0.5 h / 20 °C

5: 27 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C

With pyridine; dmap; sodium hydroxide; Dess-Martin periodane; acetic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; acetone; toluene; 5: Dess-Martin oxidation;

DOI:10.1016/j.tet.2006.05.077

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