2,4,10,15,23,25-Hexacosahexaenoic acid, 21-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-7,13,19-tris[(4-methoxyphenyl) methoxy]-6,12,14,20,22-pentamethyl-, methyl ester, (2Z,4E,6R,7R,10Z,12S,13S,14S,15Z,19R,20S,21S,22S,23Z)-

Base Information

• Chemical Name: 2,4,10,15,23,25-Hexacosahexaenoic acid, 21-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-7,13,19-tris[(4-methoxyphenyl) methoxy]-6,12,14,20,22-pentamethyl-, methyl ester, (2Z,4E,6R,7R,10Z,12S,13S,14S,15Z,19R,20S,21S,22S,23Z)-
• CAS No.: 479673-34-2
• Molecular Formula: C62H90O9Si
• Molecular Weight: 1007.48
• Mol file: 479673-34-2.mol

Synonyms:

Chemical Property of 2,4,10,15,23,25-Hexacosahexaenoic acid, 21-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-7,13,19-tris[(4-methoxyphenyl) methoxy]-6,12,14,20,22-pentamethyl-, methyl ester, (2Z,4E,6R,7R,10Z,12S,13S,14S,15Z,19R,20S,21S,22S,23Z)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,4,10,15,23,25-Hexacosahexaenoic acid, 21-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-7,13,19-tris[(4-methoxyphenyl) methoxy]-6,12,14,20,22-pentamethyl-, methyl ester, (2Z,4E,6R,7R,10Z,12S,13S,14S,15Z,19R,20S,21S,22S,23Z)-

There total 23 articles about 2,4,10,15,23,25-Hexacosahexaenoic acid, 21-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-7,13,19-tris[(4-methoxyphenyl) methoxy]-6,12,14,20,22-pentamethyl-, methyl ester, (2Z,4E,6R,7R,10Z,12S,13S,14S,15Z,19R,20S,21S,22S,23Z)- 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:

(S)-4-Benzyl-3-[(2S,3R)-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2-methyl-hexanoyl]-oxazolidin-2-one (154919-93-4) → (6R, [7R,] [12S,] 13S, [14S,] [19R,] [20R,] [21R,] 22S)-21-(TERT-BUTYLDIMETHYLSILANYLOXY)-7,13, [19-TRIS-(4-METHOXYBENZYLOXY)-6,] 12,14, 20,22-pentamethylhexacosa-2, 4,10, 15,23, 25-hexaenoic acid methyl ester (479673-34-2)

Guidance literature:

Multi-step reaction with 13 steps

1.1: LiBH₄

1.2: PPTS

2.1: 92 percent / DIBAL

3.1: Dess-Martin periodinane

4.1: NaH

5.1: 84 percent / HF*pyridine

6.1: 72 percent / Dess-Martin periodinane

7.1: 74 percent / NaHMDS

8.1: 68 percent / NaCNBH₃; TMSCl

9.1: 89 percent / Dess-Martin periodinane

10.1: 48 percent / NaHMDS

11.1: 77 percent / DIBAL

12.1: Dess-Martin periodinane

13.1: KHMDS; 18-crown-6

With lithium borohydride; chloro-trimethyl-silane; 18-crown-6 ether; sodium hexamethyldisilazane; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; sodium cyanoborohydride; Dess-Martin periodane; pyridine hydrogenfluoride; 3.1: Dess-Martin oxidation / 4.1: Wittig-Horner reaction / 6.1: Dess-Martin oxidation / 7.1: Wittig reaction / 9.1: Dess-Martin oxidation / 10.1: Wittig reaction / 12.1: Dess-Martin oxidation;

DOI:10.1021/ol026942l

Reference yield:

(4R,5R)-tert-butyl-{3-[2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]propoxy}dimethylsilane (479673-49-9) → (6R, [7R,] [12S,] 13S, [14S,] [19R,] [20R,] [21R,] 22S)-21-(TERT-BUTYLDIMETHYLSILANYLOXY)-7,13, [19-TRIS-(4-METHOXYBENZYLOXY)-6,] 12,14, 20,22-pentamethylhexacosa-2, 4,10, 15,23, 25-hexaenoic acid methyl ester (479673-34-2)

Guidance literature:

Multi-step reaction with 12 steps

1: 92 percent / DIBAL

2: Dess-Martin periodinane

3: NaH

4: 84 percent / HF*pyridine

5: 72 percent / Dess-Martin periodinane

6: 74 percent / NaHMDS

7: 68 percent / NaCNBH₃; TMSCl

8: 89 percent / Dess-Martin periodinane

9: 48 percent / NaHMDS

10: 77 percent / DIBAL

11: Dess-Martin periodinane

12: KHMDS; 18-crown-6

With chloro-trimethyl-silane; 18-crown-6 ether; sodium hexamethyldisilazane; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; sodium cyanoborohydride; Dess-Martin periodane; pyridine hydrogenfluoride; 2: Dess-Martin oxidation / 3: Wittig-Horner reaction / 5: Dess-Martin oxidation / 6: Wittig reaction / 8: Dess-Martin oxidation / 9: Wittig reaction / 11: Dess-Martin oxidation;

DOI:10.1021/ol026942l

Reference yield:

(2S,3R)-6-(tert-butyldimethylsilanyloxy)-3-(4-methoxybenzyloxy)-2-methylhexanal (479673-40-0) → (6R, [7R,] [12S,] 13S, [14S,] [19R,] [20R,] [21R,] 22S)-21-(TERT-BUTYLDIMETHYLSILANYLOXY)-7,13, [19-TRIS-(4-METHOXYBENZYLOXY)-6,] 12,14, 20,22-pentamethylhexacosa-2, 4,10, 15,23, 25-hexaenoic acid methyl ester (479673-34-2)

Guidance literature:

Multi-step reaction with 10 steps

1: NaH

2: 84 percent / HF*pyridine

3: 72 percent / Dess-Martin periodinane

4: 74 percent / NaHMDS

5: 68 percent / NaCNBH₃; TMSCl

6: 89 percent / Dess-Martin periodinane

7: 48 percent / NaHMDS

8: 77 percent / DIBAL

9: Dess-Martin periodinane

10: KHMDS; 18-crown-6

With chloro-trimethyl-silane; 18-crown-6 ether; sodium hexamethyldisilazane; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; sodium cyanoborohydride; Dess-Martin periodane; pyridine hydrogenfluoride; 1: Wittig-Horner reaction / 3: Dess-Martin oxidation / 4: Wittig reaction / 6: Dess-Martin oxidation / 7: Wittig reaction / 9: Dess-Martin oxidation;

DOI:10.1021/ol026942l

upstream raw materials:

bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate

(S)-4-Benzyl-3-[(2S,3R)-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2-methyl-hexanoyl]-oxazolidin-2-one

(R)-4-Benzyl-3-[(2R,3S,4S)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentanoyl]-oxazolidin-2-one

(E)-(4R,5R)-5-(4-Methoxy-benzyloxy)-4-methyl-8-oxo-oct-2-enoic acid ethyl ester

Downstream raw materials:

(2Z,4E,10Z,15Z,23Z)-(6R,7R,12S,13S,14S,19R,20R,21S,22S)-21-Hydroxy-7,13,19-tris-(4-methoxy-benzyloxy)-6,12,14,20,22-pentamethyl-hexacosa-2,4,10,15,23,25-hexaenoic acid methyl ester

(3Z,5E,11Z,16Z)-(7R,8R,13S,14S,15S,20R,21S,22S)-8,14,20-Tris-(4-methoxy-benzyloxy)-7,13,15,21-tetramethyl-22-((Z)-(S)-1-methyl-penta-2,4-dienyl)-oxacyclodocosa-3,5,11,16-tetraen-2-one