3-chloro-6-hydroxy-2-((S,E)-4-((4R,5R)-5-((R)-4-hydroxypentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(methoxymethoxy)but-1-enyl)-4-methoxybenzoic acid

Base Information

Chemical Name:3-chloro-6-hydroxy-2-((S,E)-4-((4R,5R)-5-((R)-4-hydroxypentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(methoxymethoxy)but-1-enyl)-4-methoxybenzoic acid
CAS No.:1427278-72-5
Molecular Formula:C₂₄H₃₅ClO₉
Molecular Weight:502.99
Hs Code.:

Synonyms:3-chloro-6-hydroxy-2-((S,E)-4-((4R,5R)-5-((R)-4-hydroxypentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(methoxymethoxy)but-1-enyl)-4-methoxybenzoic acid

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Chemical Property of 3-chloro-6-hydroxy-2-((S,E)-4-((4R,5R)-5-((R)-4-hydroxypentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(methoxymethoxy)but-1-enyl)-4-methoxybenzoic acid

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Technology Process of 3-chloro-6-hydroxy-2-((S,E)-4-((4R,5R)-5-((R)-4-hydroxypentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(methoxymethoxy)but-1-enyl)-4-methoxybenzoic acid

There total 11 articles about 3-chloro-6-hydroxy-2-((S,E)-4-((4R,5R)-5-((R)-4-hydroxypentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(methoxymethoxy)but-1-enyl)-4-methoxybenzoic 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: 80.0%

: 1427278-70-3
6-chloro-5-((S,E)-4-((4R,5R)-5-((R)-4-hydroxypentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(methoxymethoxy)but-1-enyl)-7-methoxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one

: 1427278-72-5
3-chloro-6-hydroxy-2-((S,E)-4-((4R,5R)-5-((R)-4-hydroxypentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(methoxymethoxy)but-1-enyl)-4-methoxybenzoic acid

Guidance literature:: With lithium hydroxide monohydrate; In tetrahydrofuran; water; at 0 ℃; for 24h;
DOI:10.1016/j.tet.2013.02.033

Reference yield:

: 1427278-68-9
(S)-3-(methoxymethoxy)-3-((4R,5R)-5-((R)-4-tert-butyldiphenylsilyloxypentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)propan-1-ol

: 1427278-72-5
3-chloro-6-hydroxy-2-((S,E)-4-((4R,5R)-5-((R)-4-hydroxypentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(methoxymethoxy)but-1-enyl)-4-methoxybenzoic acid

Guidance literature:: Multi-step reaction with 5 steps

1.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.5 h / -20 - 0 °C / Inert atmosphere

2.1: dihydrogen peroxide; ammonium molybdate tetrahydrate / ethanol / 6 h / 0 - 20 °C

3.1: 18-crown-6 ether; potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C / Inert atmosphere

3.2: 2 h / -78 - 20 °C / Inert atmosphere

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

5.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 24 h / 0 °C

With 18-crown-6 ether; lithium hydroxide monohydrate; ammonium molybdate tetrahydrate; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; dihydrogen peroxide; potassium hexamethylsilazane; triphenylphosphine; In tetrahydrofuran; ethanol; water; toluene; 1.1: |Mitsunobu Displacement / 3.1: |Julia-Kocienski Olefination / 3.2: |Julia-Kocienski Olefination;
DOI:10.1016/j.tet.2013.02.033

Reference yield:

: 1427278-65-6
5-((S)-3-(methoxymethoxy)-3-((4R,5R)-5-((R)-4-tert-butyldiphenylsilyloxypentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)propylsulfonyl)-1-phenyl-1H-tetrazole

: 1427278-72-5
3-chloro-6-hydroxy-2-((S,E)-4-((4R,5R)-5-((R)-4-hydroxypentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(methoxymethoxy)but-1-enyl)-4-methoxybenzoic acid

Guidance literature:: Multi-step reaction with 3 steps

1.1: 18-crown-6 ether; potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C / Inert atmosphere

1.2: 2 h / -78 - 20 °C / Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

3.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 24 h / 0 °C

With 18-crown-6 ether; lithium hydroxide monohydrate; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; In tetrahydrofuran; water; toluene; 1.1: |Julia-Kocienski Olefination / 1.2: |Julia-Kocienski Olefination;
DOI:10.1016/j.tet.2013.02.033