(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

Base Information

• Chemical Name: (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
• CAS No.: 909016-48-4
• Molecular Formula: C₃₇H₄₇BrO₆Si
• Molecular Weight: 695.766
• Mol file: 909016-48-4.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 22 articles about (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 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:

(S)-2-(2-Benzyloxy-1,1-dimethyl-ethyl)-oxirane (111080-21-8) → (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:

Multi-step reaction with 17 steps

1: 85 percent / nBuLi / tetrahydrofuran; hexane / -78 - -20 °C

2: 1.) (CF₃CO₂)2IPh; 2.) H₂O, AcOH / 1.) MeOH, 0 deg C; 2.) THF, r.t.

3: Me₄NBH(OAc)3 / acetic acid; acetonitrile / -40 - -20 °C

4: CSA / acetone / Ambient temperature

5: 1.) OsO₄, NMO; 2.) NaIO₄ / 1.) acetone, tBuOH, r.t.; 2.) H₂O, r.t.

6: LDA / tetrahydrofuran; hexane / -78 °C

7: 1.) DMSO, (COCl)2; 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C; 2.) -78 deg C -> 0 deg C

8: 89 percent / PPTS / methanol / 50 °C

9: imidazole / dimethylformamide / 0 °C

10: H₂ / Pd(OH)2/C / dioxane / Ambient temperature

11: DMSO, SO₃*Py, Et₃N / Ambient temperature

12: 98 percent

13: LiOH / tetrahydrofuran; methanol; H₂O / 50 - 75 °C

15: 1.) DMSO, (COCl)2; 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C; 2.)-78 deg C -> 0 deg C

16: NaN(SiMe₃)2 / tetrahydrofuran / -78 °C

17: I₂ / benzene / Ambient temperature

With 1H-imidazole; lithium hydroxide; sodium periodate; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; oxalyl dichloride; pyridine-SO₃ complex; camphor-10-sulfonic acid; water; hydrogen; iodine; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; acetic acid; dimethyl sulfoxide; triethylamine; bis-[(trifluoroacetoxy)iodo]benzene; tetramethylammonium triacetoxyborohydride; lithium diisopropyl amide; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; water; acetic acid; N,N-dimethyl-formamide; acetone; acetonitrile; benzene;

DOI:10.1246/cl.1998.85

Reference yield:

(3R,5S)-1-(benzyloxy)-2,2-dimethyloct-7-ene-3,5-diol (909016-29-1) → (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:

Multi-step reaction with 14 steps

1: CSA / acetone / Ambient temperature

2: 1.) OsO₄, NMO; 2.) NaIO₄ / 1.) acetone, tBuOH, r.t.; 2.) H₂O, r.t.

3: LDA / tetrahydrofuran; hexane / -78 °C

4: 1.) DMSO, (COCl)2; 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C; 2.) -78 deg C -> 0 deg C

5: 89 percent / PPTS / methanol / 50 °C

6: imidazole / dimethylformamide / 0 °C

7: H₂ / Pd(OH)2/C / dioxane / Ambient temperature

8: DMSO, SO₃*Py, Et₃N / Ambient temperature

9: 98 percent

10: LiOH / tetrahydrofuran; methanol; H₂O / 50 - 75 °C

12: 1.) DMSO, (COCl)2; 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C; 2.)-78 deg C -> 0 deg C

13: NaN(SiMe₃)2 / tetrahydrofuran / -78 °C

14: I₂ / benzene / Ambient temperature

With 1H-imidazole; lithium hydroxide; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; pyridine-SO₃ complex; camphor-10-sulfonic acid; hydrogen; iodine; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; water; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1246/cl.1998.85

upstream raw materials:

(S)-2-(2-Benzyloxy-1,1-dimethyl-ethyl)-oxirane

(3R,5S)-1-(benzyloxy)-2,2-dimethyloct-7-ene-3,5-diol

(R)-8-Benzyloxy-6-hydroxy-7,7-dimethyl-oct-1-en-4-one

(4S,6R)-4-Allyl-6-(2-benzyloxy-1,1-dimethyl-ethyl)-2,2-dimethyl-[1,3]dioxane