(9E,15E)-(1R,5S,6R,8R,11S,17R)-1,11-Dihydroxy-5-((1R,3R,4S,5S)-4-hydroxy-1,3,5-trimethyl-6-oxo-octyl)-6,8,16,18-tetramethyl-4,21-dioxa-bicyclo[15.3.1]henicosa-9,15,18-trien-3-one

Base Information

• Chemical Name: (9E,15E)-(1R,5S,6R,8R,11S,17R)-1,11-Dihydroxy-5-((1R,3R,4S,5S)-4-hydroxy-1,3,5-trimethyl-6-oxo-octyl)-6,8,16,18-tetramethyl-4,21-dioxa-bicyclo[15.3.1]henicosa-9,15,18-trien-3-one
• CAS No.: 106927-20-2
• Molecular Formula: C₃₄H₅₆O₇
• Molecular Weight: 576.814
• Mol file: 106927-20-2.mol

Synonyms:

Chemical Property of (9E,15E)-(1R,5S,6R,8R,11S,17R)-1,11-Dihydroxy-5-((1R,3R,4S,5S)-4-hydroxy-1,3,5-trimethyl-6-oxo-octyl)-6,8,16,18-tetramethyl-4,21-dioxa-bicyclo[15.3.1]henicosa-9,15,18-trien-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (9E,15E)-(1R,5S,6R,8R,11S,17R)-1,11-Dihydroxy-5-((1R,3R,4S,5S)-4-hydroxy-1,3,5-trimethyl-6-oxo-octyl)-6,8,16,18-tetramethyl-4,21-dioxa-bicyclo[15.3.1]henicosa-9,15,18-trien-3-one

There total 19 articles about (9E,15E)-(1R,5S,6R,8R,11S,17R)-1,11-Dihydroxy-5-((1R,3R,4S,5S)-4-hydroxy-1,3,5-trimethyl-6-oxo-octyl)-6,8,16,18-tetramethyl-4,21-dioxa-bicyclo[15.3.1]henicosa-9,15,18-trien-3-one 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:

(5R,6S)-6-((1R,3R)-1,3-Dimethyl-pent-4-enyl)-5-methyl-tetrahydro-pyran-2-one (129117-26-6) → (9E,15E)-(1R,5S,6R,8R,11S,17R)-1,11-Dihydroxy-5-((1R,3R,4S,5S)-4-hydroxy-1,3,5-trimethyl-6-oxo-octyl)-6,8,16,18-tetramethyl-4,21-dioxa-bicyclo[15.3.1]henicosa-9,15,18-trien-3-one (33538-64-6,106927-20-2)

Guidance literature:

Multi-step reaction with 14 steps

1: LDA / hexamethylphosphoric acid triamide / -78 °C

2: 1.) LiAlH₄ 2.) imidazole 3.) pyridine / 3.) HMPA

3: 1.) O₃/Me₂S

4: 1.) PPTS 2.) O₃/Me₂S 4.) PDC/Zeolite 3A

5: 1.) PPTS 2.) tetramethylammonium triacetoxyborohydride / 1.) MeOH

6: 93 percent / CSA

7: DIBAH

8: 1.) 2,4,6-trichlorobenzoyl chloride/Et₃N 2.) 2/DMAP

9: 68 percent / n-Bu₄NF*3H₂O

10: 1.) PDC/Zeolite 3A 2.) K₂CO₃/18-Crown-6 / 2.) toluene, r.t.

11: 55 percent / NaBH₄-CeCl₃

12: 1.) pyridine 2.) PPTS / 1.) DMAP 2.) MeOH

13: RuCl₂(PPh₃)3/K₂CO₃

14: 1.) K₂CO₃ 2.) AcOH/H₂O(4:1) / 1.) MeOH

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; dipyridinium dichromate; tris(triphenylphosphine)ruthenium(II) chloride; cerium(III) chloride; 18-crown-6 ether; dimethylsulfide; Zeolite 3A; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; ozone; acetic acid; triethylamine; tetramethylammonium triacetoxyborohydride; lithium diisopropyl amide; In N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1016/S0040-4039(00)88867-X

Reference yield:

tert-Butyl-[(1R,2R,4R)-1-((S)-2-iodo-1-methyl-ethyl)-2,4-dimethyl-hex-5-enyloxy]-dimethyl-silane (129117-24-4) → (9E,15E)-(1R,5S,6R,8R,11S,17R)-1,11-Dihydroxy-5-((1R,3R,4S,5S)-4-hydroxy-1,3,5-trimethyl-6-oxo-octyl)-6,8,16,18-tetramethyl-4,21-dioxa-bicyclo[15.3.1]henicosa-9,15,18-trien-3-one (33538-64-6,106927-20-2)

Guidance literature:

Multi-step reaction with 16 steps

1: 68 percent / LDA

2: 93 percent / CF₃COOH

3: LDA / hexamethylphosphoric acid triamide / -78 °C

4: 1.) LiAlH₄ 2.) imidazole 3.) pyridine / 3.) HMPA

5: 1.) O₃/Me₂S

6: 1.) PPTS 2.) O₃/Me₂S 4.) PDC/Zeolite 3A

7: 1.) PPTS 2.) tetramethylammonium triacetoxyborohydride / 1.) MeOH

8: 93 percent / CSA

9: DIBAH

10: 1.) 2,4,6-trichlorobenzoyl chloride/Et₃N 2.) 2/DMAP

11: 68 percent / n-Bu₄NF*3H₂O

12: 1.) PDC/Zeolite 3A 2.) K₂CO₃/18-Crown-6 / 2.) toluene, r.t.

13: 55 percent / NaBH₄-CeCl₃

14: 1.) pyridine 2.) PPTS / 1.) DMAP 2.) MeOH

15: RuCl₂(PPh₃)3/K₂CO₃

16: 1.) K₂CO₃ 2.) AcOH/H₂O(4:1) / 1.) MeOH

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; dipyridinium dichromate; tris(triphenylphosphine)ruthenium(II) chloride; cerium(III) chloride; 18-crown-6 ether; dimethylsulfide; Zeolite 3A; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; ozone; acetic acid; triethylamine; trifluoroacetic acid; tetramethylammonium triacetoxyborohydride; lithium diisopropyl amide; In N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1016/S0040-4039(00)88867-X

Reference yield:

(2R,3R,4R,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-oct-7-en-1-ol (129117-23-3) → (9E,15E)-(1R,5S,6R,8R,11S,17R)-1,11-Dihydroxy-5-((1R,3R,4S,5S)-4-hydroxy-1,3,5-trimethyl-6-oxo-octyl)-6,8,16,18-tetramethyl-4,21-dioxa-bicyclo[15.3.1]henicosa-9,15,18-trien-3-one (33538-64-6,106927-20-2)

Guidance literature:

Multi-step reaction with 17 steps

1: 1.) MeCl/ET₃N 2.) NaI

2: 68 percent / LDA

3: 93 percent / CF₃COOH

4: LDA / hexamethylphosphoric acid triamide / -78 °C

5: 1.) LiAlH₄ 2.) imidazole 3.) pyridine / 3.) HMPA

6: 1.) O₃/Me₂S

7: 1.) PPTS 2.) O₃/Me₂S 4.) PDC/Zeolite 3A

8: 1.) PPTS 2.) tetramethylammonium triacetoxyborohydride / 1.) MeOH

9: 93 percent / CSA

10: DIBAH

11: 1.) 2,4,6-trichlorobenzoyl chloride/Et₃N 2.) 2/DMAP

12: 68 percent / n-Bu₄NF*3H₂O

13: 1.) PDC/Zeolite 3A 2.) K₂CO₃/18-Crown-6 / 2.) toluene, r.t.

14: 55 percent / NaBH₄-CeCl₃

15: 1.) pyridine 2.) PPTS / 1.) DMAP 2.) MeOH

16: RuCl₂(PPh₃)3/K₂CO₃

17: 1.) K₂CO₃ 2.) AcOH/H₂O(4:1) / 1.) MeOH

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; dipyridinium dichromate; tris(triphenylphosphine)ruthenium(II) chloride; cerium(III) chloride; 18-crown-6 ether; methylene chloride; dimethylsulfide; Zeolite 3A; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; ozone; acetic acid; triethylamine; trifluoroacetic acid; sodium iodide; tetramethylammonium triacetoxyborohydride; lithium diisopropyl amide; In N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1016/S0040-4039(00)88867-X

upstream raw materials:

Acetic acid (9E,15E)-(1R,5S,6R,8R,11S,17R)-5-((1R,3R,4S,5S)-4-hydroxy-1,3,5-trimethyl-6-oxo-octyl)-1-methoxy-6,8,16,18-tetramethyl-3-oxo-4,21-dioxa-bicyclo[15.3.1]henicosa-9,15,18-trien-11-yl ester

(5R,6S)-6-((1R,3R)-1,3-Dimethyl-pent-4-enyl)-5-methyl-tetrahydro-pyran-2-one

tert-Butyl-[(1R,2R,4R)-1-((S)-2-iodo-1-methyl-ethyl)-2,4-dimethyl-hex-5-enyloxy]-dimethyl-silane

(2R,3R,4R,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-oct-7-en-1-ol