Oxacyclodocosa-11,16-dien-2-one, 14,20-bis[(4-methoxyphenyl)methoxy]-13,15,21-trimethyl-22-[(1S,2Z)-1- methyl-2,4-pentadienyl]-, (11Z,13S,14S,15S,16Z,20R,21S,22S)-

Base Information

• Chemical Name: Oxacyclodocosa-11,16-dien-2-one, 14,20-bis[(4-methoxyphenyl)methoxy]-13,15,21-trimethyl-22-[(1S,2Z)-1- methyl-2,4-pentadienyl]-, (11Z,13S,14S,15S,16Z,20R,21S,22S)-
• CAS No.: 479673-47-7
• Molecular Formula: C46H66O6
• Molecular Weight: 715.026
• Mol file: 479673-47-7.mol

Synonyms:

Chemical Property of Oxacyclodocosa-11,16-dien-2-one, 14,20-bis[(4-methoxyphenyl)methoxy]-13,15,21-trimethyl-22-[(1S,2Z)-1- methyl-2,4-pentadienyl]-, (11Z,13S,14S,15S,16Z,20R,21S,22S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Oxacyclodocosa-11,16-dien-2-one, 14,20-bis[(4-methoxyphenyl)methoxy]-13,15,21-trimethyl-22-[(1S,2Z)-1- methyl-2,4-pentadienyl]-, (11Z,13S,14S,15S,16Z,20R,21S,22S)-

There total 22 articles about Oxacyclodocosa-11,16-dien-2-one, 14,20-bis[(4-methoxyphenyl)methoxy]-13,15,21-trimethyl-22-[(1S,2Z)-1- methyl-2,4-pentadienyl]-, (11Z,13S,14S,15S,16Z,20R,21S,22S)- 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: 57.0%

(10Z,15Z,23Z)-(12S,13S,14S,19R,20R,21S,22S)-21-Hydroxy-13,19-bis-(4-methoxy-benzyloxy)-12,14,20,22-tetramethyl-hexacosa-10,15,23,25-tetraenoic acid (479673-46-6) → (11Z,16Z)-(13S,14S,15S,20R,21S,22S)-14,20-Bis-(4-methoxy-benzyloxy)-13,15,21-trimethyl-22-((Z)-(S)-1-methyl-penta-2,4-dienyl)-oxacyclodocosa-11,16-dien-2-one (479673-47-7)

Guidance literature:

With 2,4,6-trichlorobenzoyl chloride;

DOI:10.1021/ol026942l

Reference yield:

(S)-4-Benzyl-3-[(2S,3R)-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2-methyl-hexanoyl]-oxazolidin-2-one (154919-93-4) → (11Z,16Z)-(13S,14S,15S,20R,21S,22S)-14,20-Bis-(4-methoxy-benzyloxy)-13,15,21-trimethyl-22-((Z)-(S)-1-methyl-penta-2,4-dienyl)-oxacyclodocosa-11,16-dien-2-one (479673-47-7)

Guidance literature:

Multi-step reaction with 17 steps

1.1: LiBH₄

1.2: PPTS

2.1: 92 percent / DIBAL

3.1: Dess-Martin periodinane

4.1: 85 percent / LDA

5.1: 88 percent / 2,6-lutidine

6.1: 79 percent / DIBAL

7.1: Dess-Martin periodinane

8.1: CrCl₂

8.2: NaH

9.1: 88 percent / HF*pyridine / pyridine

10.1: I₂; PPh₃; imidazole

11.1: NaHMDS

12.1: 78 percent / HF*pyridine / pyridine

13.1: Dess-Martin periodinane

14.1: NaClO₂; 2-methyl-2-butene; NaH₂PO₄

15.1: 57 percent / TBAF

16.1: 57 percent / 2,4,6-trichlorobenzoyl chloride

With 1H-imidazole; 2,6-dimethylpyridine; chromium dichloride; sodium chlorite; sodium dihydrogenphosphate; lithium borohydride; 2-methyl-but-2-ene; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; iodine; sodium hexamethyldisilazane; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; triphenylphosphine; lithium diisopropyl amide; In pyridine; 3.1: Dess-Martin oxidation / 7.1: Dess-Martin oxidation / 8.1: Peterson olefination / 8.2: Peterson olefination / 12.1: Wittig reaction / 14.1: Dess-Martin oxidation / 17.1: Yamaguchi reaction;

DOI:10.1021/ol026942l

Reference yield:

1,10-Decanediol (112-47-0) → (11Z,16Z)-(13S,14S,15S,20R,21S,22S)-14,20-Bis-(4-methoxy-benzyloxy)-13,15,21-trimethyl-22-((Z)-(S)-1-methyl-penta-2,4-dienyl)-oxacyclodocosa-11,16-dien-2-one (479673-47-7)

Guidance literature:

Multi-step reaction with 11 steps

1: 42 percent / NaH

2: 80 percent / Dess-Martin periodinane

3: 75 percent / NaHMDS

4: 70 percent / DIBAL

5: Dess-Martin periodinane

6: NaHMDS

7: 78 percent / HF*pyridine / pyridine

8: Dess-Martin periodinane

9: NaClO₂; 2-methyl-2-butene; NaH₂PO₄

10: 57 percent / TBAF

11: 57 percent / 2,4,6-trichlorobenzoyl chloride

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; In pyridine; 2: Dess-Martin oxidation / 3: Wittig reaction / 5: Dess-Martin oxidation / 6: Wittig reaction / 8: Dess-Martin oxidation / 11: Yamaguchi reaction;

DOI:10.1021/ol026942l

upstream raw materials:

(10Z,15Z,23Z)-(12S,13S,14S,19R,20R,21S,22S)-21-Hydroxy-13,19-bis-(4-methoxy-benzyloxy)-12,14,20,22-tetramethyl-hexacosa-10,15,23,25-tetraenoic acid

1,10-Decanediol

10-(tert-butyldimethylsilyl)oxydecan-1-ol

10-(tert-butyldimethylsilanyloxy)decanal