(2S,3S,4R)-2,3,5-tris(4-methoxybenzyloxy)-4-[[(2E,4R,6E,8E,10S,11R,12S)-1,5-dioxo-2,4,6,8,10,12-hexamethyl-11-(4-methoxybenzyloxy)-2,6,8-docosatrienyl]oxy]pentanoic acid

Base Information

Chemical Name:(2S,3S,4R)-2,3,5-tris(4-methoxybenzyloxy)-4-[[(2E,4R,6E,8E,10S,11R,12S)-1,5-dioxo-2,4,6,8,10,12-hexamethyl-11-(4-methoxybenzyloxy)-2,6,8-docosatrienyl]oxy]pentanoic acid
CAS No.:361525-10-2
Molecular Formula:C₆₅H₈₈O₁₃
Molecular Weight:1077.41
Hs Code.:

(2S,3S,4R)-2,3,5-tris(4-methoxybenzyloxy)-4-[[(2E,4R,6E,8E,10S,11R,12S)-1,5-dioxo-2,4,6,8,10,12-hexamethyl-11-(4-methoxybenzyloxy)-2,6,8-docosatrienyl]oxy]pentanoic acid

Synonyms:(2S,3S,4R)-2,3,5-tris(4-methoxybenzyloxy)-4-[[(2E,4R,6E,8E,10S,11R,12S)-1,5-dioxo-2,4,6,8,10,12-hexamethyl-11-(4-methoxybenzyloxy)-2,6,8-docosatrienyl]oxy]pentanoic acid

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Chemical Property of (2S,3S,4R)-2,3,5-tris(4-methoxybenzyloxy)-4-[[(2E,4R,6E,8E,10S,11R,12S)-1,5-dioxo-2,4,6,8,10,12-hexamethyl-11-(4-methoxybenzyloxy)-2,6,8-docosatrienyl]oxy]pentanoic acid

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Technology Process of (2S,3S,4R)-2,3,5-tris(4-methoxybenzyloxy)-4-[[(2E,4R,6E,8E,10S,11R,12S)-1,5-dioxo-2,4,6,8,10,12-hexamethyl-11-(4-methoxybenzyloxy)-2,6,8-docosatrienyl]oxy]pentanoic acid

There total 44 articles about (2S,3S,4R)-2,3,5-tris(4-methoxybenzyloxy)-4-[[(2E,4R,6E,8E,10S,11R,12S)-1,5-dioxo-2,4,6,8,10,12-hexamethyl-11-(4-methoxybenzyloxy)-2,6,8-docosatrienyl]oxy]pentanoic 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:

: 443305-05-3
(2E,6E,8E)-(4R,10S,11R,12S)-11-(4-Methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-5-oxo-docosa-2,6,8-trienoic acid (1R,2R,3S)-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-4-oxo-butyl ester

: 361525-10-2
(2S,3S,4R)-2,3,5-tris(4-methoxybenzyloxy)-4-[[(2E,4R,6E,8E,10S,11R,12S)-1,5-dioxo-2,4,6,8,10,12-hexamethyl-11-(4-methoxybenzyloxy)-2,6,8-docosatrienyl]oxy]pentanoic acid

Guidance literature:: With sodium chlorite;
DOI:10.1055/s-2002-22726

Reference yield:

: 532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7
D-arabinofuranose

: 361525-10-2
(2S,3S,4R)-2,3,5-tris(4-methoxybenzyloxy)-4-[[(2E,4R,6E,8E,10S,11R,12S)-1,5-dioxo-2,4,6,8,10,12-hexamethyl-11-(4-methoxybenzyloxy)-2,6,8-docosatrienyl]oxy]pentanoic acid

Guidance literature:: Multi-step reaction with 9 steps

1: H₂SO₄ / dimethylformamide / 90 °C

2: Bu₄NBr; KOH / tetrahydrofuran; H₂O / 90 °C

3: 95 percent / DIBAL; NiCl₂(dppp) / diethyl ether / 20 °C

4: LiAlH₄ / tetrahydrofuran / 20 °C

5: 93 percent / triethylamine / CH₂Cl₂ / 20 h / 20 °C

6: DCC; DMAP; DMAP*HCl / CH₂Cl₂ / 12 h / Heating

7: 336 mg / aq. HCl / tetrahydrofuran / 12 h / 20 °C

8: Dess-Martin periodinane; pyridine / CH₂Cl₂ / 2 h / 20 °C

9: 265 mg / NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 20 h / 20 °C

With pyridine; hydrogenchloride; dmap; potassium hydroxide; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; 2-methyl-but-2-ene; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); tetrabutylammomium bromide; 4-(dimethylamino)pyridine hydrochloride; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; dicyclohexyl-carbodiimide; sulfuric acid; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 6: Keck's reaction;
DOI:10.1021/ja0057272

Reference yield:

: 331626-81-4
(2R,3R,4R)-5-(tert-Butyl-dimethyl-silanyloxy)-1,3,4-tris-(4-methoxy-benzyloxy)-pentan-2-ol

: 361525-10-2
(2S,3S,4R)-2,3,5-tris(4-methoxybenzyloxy)-4-[[(2E,4R,6E,8E,10S,11R,12S)-1,5-dioxo-2,4,6,8,10,12-hexamethyl-11-(4-methoxybenzyloxy)-2,6,8-docosatrienyl]oxy]pentanoic acid

Guidance literature:: Multi-step reaction with 5 steps

1.1: 79 percent / DCC; DMAP; DMAP*HCl

2.1: 9-BBN / tetrahydrofuran / 12 h / 20 °C

2.2: 84 percent / aq. K₃PO₄ / PdCl₂(dppf) / tetrahydrofuran / 0.5 h / 70 °C

3.1: 84 percent / aq. HCl / tetrahydrofuran

4.1: Dess-Martin periodinane

5.1: NaClO₂

With hydrogenchloride; dmap; sodium chlorite; 9-borabicyclo[3.3.1]nonane dimer; 4-(dimethylamino)pyridine hydrochloride; Dess-Martin periodane; dicyclohexyl-carbodiimide; In tetrahydrofuran; 2.2: Suzuki reaction;
DOI:10.1055/s-2002-22726