Technology Process of 2,8,13,21,23-Tetracosapentaenoic acid,
19-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5,11,17-tris[(4-methoxyphenyl)
methoxy]-4,10,12,18,20-pentamethyl-, ethyl ester,
(2E,4R,5R,8Z,10S,11S,12S,13Z,17R,18S,19S,20S,21Z)-
There total 22 articles about 2,8,13,21,23-Tetracosapentaenoic acid,
19-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5,11,17-tris[(4-methoxyphenyl)
methoxy]-4,10,12,18,20-pentamethyl-, ethyl ester,
(2E,4R,5R,8Z,10S,11S,12S,13Z,17R,18S,19S,20S,21Z)- 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:
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479673-33-1
(4R, [5R,] 10S, [11S,] 12S, [17R,] [18R,] [19R,] 205)-19-(TERT-BUTYLDIMETHYLSILANYLOXY)-5,11, [17-TRIS-(4-METHOXYBENZYLOXY)-4, 10,] 12,18, 20-pentamethyltetracosa-2,8, 13, 21,23-pentaenoic acid ethyl ester
- Guidance literature:
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With
sodium hexamethyldisilazane;
DOI:10.1021/ol026942l
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479673-33-1
(4R, [5R,] 10S, [11S,] 12S, [17R,] [18R,] [19R,] 205)-19-(TERT-BUTYLDIMETHYLSILANYLOXY)-5,11, [17-TRIS-(4-METHOXYBENZYLOXY)-4, 10,] 12,18, 20-pentamethyltetracosa-2,8, 13, 21,23-pentaenoic acid ethyl ester
- Guidance literature:
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Multi-step reaction with 10 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
With
lithium borohydride; chloro-trimethyl-silane; sodium hexamethyldisilazane; 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;
DOI:10.1021/ol026942l
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-
479673-33-1
(4R, [5R,] 10S, [11S,] 12S, [17R,] [18R,] [19R,] 205)-19-(TERT-BUTYLDIMETHYLSILANYLOXY)-5,11, [17-TRIS-(4-METHOXYBENZYLOXY)-4, 10,] 12,18, 20-pentamethyltetracosa-2,8, 13, 21,23-pentaenoic acid ethyl ester
- Guidance literature:
-
Multi-step reaction with 9 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
With
chloro-trimethyl-silane; sodium hexamethyldisilazane; 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;
DOI:10.1021/ol026942l