(2E,9E,11E,18E,20E,22E)-(5S,7R,8R,13S,15R,16S,17R)-7,13-Bis-benzyloxy-5-(2-benzyloxy-ethyl)-15-hydroxy-17-methoxy-8,12,16,18,22-pentamethyl-23-(2-methyl-oxazol-4-yl)-tricosa-2,9,11,18,20,22-hexaenoic acid

Base Information

• Chemical Name: (2E,9E,11E,18E,20E,22E)-(5S,7R,8R,13S,15R,16S,17R)-7,13-Bis-benzyloxy-5-(2-benzyloxy-ethyl)-15-hydroxy-17-methoxy-8,12,16,18,22-pentamethyl-23-(2-methyl-oxazol-4-yl)-tricosa-2,9,11,18,20,22-hexaenoic acid
• CAS No.: 544429-45-0
• Molecular Formula: C₅₆H₇₁NO₈
• Molecular Weight: 886.182
• Mol file: 544429-45-0.mol

Synonyms:(2E,9E,11E,18E,20E,22E)-(5S,7R,8R,13S,15R,16S,17R)-7,13-Bis-benzyloxy-5-(2-benzyloxy-ethyl)-15-hydroxy-17-methoxy-8,12,16,18,22-pentamethyl-23-(2-methyl-oxazol-4-yl)-tricosa-2,9,11,18,20,22-hexaenoic acid

Chemical Property of (2E,9E,11E,18E,20E,22E)-(5S,7R,8R,13S,15R,16S,17R)-7,13-Bis-benzyloxy-5-(2-benzyloxy-ethyl)-15-hydroxy-17-methoxy-8,12,16,18,22-pentamethyl-23-(2-methyl-oxazol-4-yl)-tricosa-2,9,11,18,20,22-hexaenoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,9E,11E,18E,20E,22E)-(5S,7R,8R,13S,15R,16S,17R)-7,13-Bis-benzyloxy-5-(2-benzyloxy-ethyl)-15-hydroxy-17-methoxy-8,12,16,18,22-pentamethyl-23-(2-methyl-oxazol-4-yl)-tricosa-2,9,11,18,20,22-hexaenoic acid

There total 48 articles about (2E,9E,11E,18E,20E,22E)-(5S,7R,8R,13S,15R,16S,17R)-7,13-Bis-benzyloxy-5-(2-benzyloxy-ethyl)-15-hydroxy-17-methoxy-8,12,16,18,22-pentamethyl-23-(2-methyl-oxazol-4-yl)-tricosa-2,9,11,18,20,22-hexaenoic acid 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: 69.0%

4-Nitro-benzoic acid (4E,6E,13E)-(1R,3S,8R,9R,11S)-3,9-bis-benzyloxy-11-(2-benzyloxy-ethyl)-14-ethoxycarbonyl-1-[(3E,5E,7E)-(1S,2R)-2-methoxy-1,3,7-trimethyl-8-(2-methyl-oxazol-4-yl)-octa-3,5,7-trienyl]-4,8-dimethyl-tetradeca-4,6,13-trienyl ester → (2E,9E,11E,18E,20E,22E)-(5S,7R,8R,13S,15R,16S,17R)-7,13-Bis-benzyloxy-5-(2-benzyloxy-ethyl)-15-hydroxy-17-methoxy-8,12,16,18,22-pentamethyl-23-(2-methyl-oxazol-4-yl)-tricosa-2,9,11,18,20,22-hexaenoic acid (544429-45-0)

Guidance literature:

With potassium trimethylsilonate;

DOI:10.1021/jo034011x

Reference yield:

(E)-4-(t-butyl-dimethyl-silanyloxy)-2-methyl-but-2-enal (144950-82-3) → (2E,9E,11E,18E,20E,22E)-(5S,7R,8R,13S,15R,16S,17R)-7,13-Bis-benzyloxy-5-(2-benzyloxy-ethyl)-15-hydroxy-17-methoxy-8,12,16,18,22-pentamethyl-23-(2-methyl-oxazol-4-yl)-tricosa-2,9,11,18,20,22-hexaenoic acid (544429-45-0)

Guidance literature:

Multi-step reaction with 19 steps

1.1: diisopropylamine; n-BuLi / tetrahydrofuran / 1 h / -78 °C

1.2: 78 percent / tetrahydrofuran / 0.08 h

2.1: (-)-diisopropyl tartrate; Ti(O-iPr)4; tert-butylhydroperoxide / molecular sieves 3 Angstroem / CH₂Cl₂ / 20 h / -20 °C

2.2: 40 percent / FeSO₄; citric acid / H₂O; CH₂Cl₂

3.1: 76 percent / TfOH

4.1: DIBAL-H

5.1: dibutylboron triflate; diisopropylethylamine / CH₂Cl₂ / 0.25 h / 0 °C

5.2: CH₂Cl₂ / 3 h / -78 °C

5.3: 89 percent / sodium acetate; hydrogen peroxide / methanol; CH₂Cl₂; H₂O / 1.5 h / 0 °C

6.1: 95 percent / trimethylaluminum / hexane; tetrahydrofuran / 0 - 20 °C

7.1: 100 percent / triethylamine / CH₂Cl₂ / 15 h / Heating

8.1: 93 percent / diisobutylaluminum hydride / tetrahydrofuran; toluene / 0.75 h / -78 °C

9.1: tert-butyllithium / tetrahydrofuran; pentane / 0.75 h / -78 °C

9.2: 89 percent / tetrahydrofuran; pentane / 0.25 h / -78 °C

10.1: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

11.1: barium hydroxide octahydrate / tetrahydrofuran / 0.5 h / 20 °C

11.2: 65 percent / tetrahydrofuran; H₂O / 16.5 h

12.1: 89 percent / citric acid / tetrahydrofuran; methanol / 1 h / 20 °C

13.1: 76 percent / diethylmethoxyborane; sodium borohydride / tetrahydrofuran; methanol / 3 h / -78 °C

14.1: 63 percent / NaH / tetrahydrofuran / 17 h / -78 - 20 °C

15.1: 82 percent / pyridine; 4-(dimethylamino)pyridine / 7 h

16.1: 87 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 0 - 20 °C

17.1: Dess-Martin periodinane

18.1: 50 percent / LiHMDS

19.1: 69 percent / TMSO^(1-)*K⁽¹⁺⁾

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; n-butyllithium; barium hydroxide octahydrate; (-)-diisopropyl tartrate; trifluorormethanesulfonic acid; di-n-butylboryl trifluoromethanesulfonate; diethyl methoxy borane; potassium trimethylsilonate; tetrabutyl ammonium fluoride; trimethylaluminum; tert.-butyl lithium; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; diisopropylamine; N-ethyl-N,N-diisopropylamine; citric acid; lithium hexamethyldisilazane; 3 A molecular sieve; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; pentane;

DOI:10.1021/jo034011x

Reference yield:

methyl (4E)-6-[(t-butyldimethylsilyl)oxy]-4-methyl-3-hydroxy-4-hexenoate (237735-58-9) → (2E,9E,11E,18E,20E,22E)-(5S,7R,8R,13S,15R,16S,17R)-7,13-Bis-benzyloxy-5-(2-benzyloxy-ethyl)-15-hydroxy-17-methoxy-8,12,16,18,22-pentamethyl-23-(2-methyl-oxazol-4-yl)-tricosa-2,9,11,18,20,22-hexaenoic acid (544429-45-0)

Guidance literature:

Multi-step reaction with 18 steps

1.1: (-)-diisopropyl tartrate; Ti(O-iPr)4; tert-butylhydroperoxide / molecular sieves 3 Angstroem / CH₂Cl₂ / 20 h / -20 °C

1.2: 40 percent / FeSO₄; citric acid / H₂O; CH₂Cl₂

2.1: 76 percent / TfOH

3.1: DIBAL-H

4.1: dibutylboron triflate; diisopropylethylamine / CH₂Cl₂ / 0.25 h / 0 °C

4.2: CH₂Cl₂ / 3 h / -78 °C

4.3: 89 percent / sodium acetate; hydrogen peroxide / methanol; CH₂Cl₂; H₂O / 1.5 h / 0 °C

5.1: 95 percent / trimethylaluminum / hexane; tetrahydrofuran / 0 - 20 °C

6.1: 100 percent / triethylamine / CH₂Cl₂ / 15 h / Heating

7.1: 93 percent / diisobutylaluminum hydride / tetrahydrofuran; toluene / 0.75 h / -78 °C

8.1: tert-butyllithium / tetrahydrofuran; pentane / 0.75 h / -78 °C

8.2: 89 percent / tetrahydrofuran; pentane / 0.25 h / -78 °C

9.1: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

10.1: barium hydroxide octahydrate / tetrahydrofuran / 0.5 h / 20 °C

10.2: 65 percent / tetrahydrofuran; H₂O / 16.5 h

11.1: 89 percent / citric acid / tetrahydrofuran; methanol / 1 h / 20 °C

12.1: 76 percent / diethylmethoxyborane; sodium borohydride / tetrahydrofuran; methanol / 3 h / -78 °C

13.1: 63 percent / NaH / tetrahydrofuran / 17 h / -78 - 20 °C

14.1: 82 percent / pyridine; 4-(dimethylamino)pyridine / 7 h

15.1: 87 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 0 - 20 °C

16.1: Dess-Martin periodinane

17.1: 50 percent / LiHMDS

18.1: 69 percent / TMSO^(1-)*K⁽¹⁺⁾

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; barium hydroxide octahydrate; (-)-diisopropyl tartrate; trifluorormethanesulfonic acid; di-n-butylboryl trifluoromethanesulfonate; diethyl methoxy borane; potassium trimethylsilonate; tetrabutyl ammonium fluoride; trimethylaluminum; tert.-butyl lithium; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; citric acid; lithium hexamethyldisilazane; 3 A molecular sieve; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; pentane;

DOI:10.1021/jo034011x

upstream raw materials:

4-(benzyloxy)butanoic acid

benzyl bromide

2-methyl-1,3-oxazole-4-carbaldehyde

(1'E,3'E)-2-methyl-4-(2'-methyl-5'-oxo-1',3'-pentadienyl)-oxazole

Refernces