4-{(4S,5R)-5-[(1E,3E,7E)-(S)-10-(4-Fluoro-phenoxy)-9-hydroxy-deca-1,3,7-trien-5-ynyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-butyric acid methyl ester

Base Information

Chemical Name:4-{(4S,5R)-5-[(1E,3E,7E)-(S)-10-(4-Fluoro-phenoxy)-9-hydroxy-deca-1,3,7-trien-5-ynyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-butyric acid methyl ester
CAS No.:620973-14-0
Molecular Formula:C₂₆H₃₁FO₆
Molecular Weight:458.527
Hs Code.:

Synonyms:4-{(4S,5R)-5-[(1E,3E,7E)-(S)-10-(4-Fluoro-phenoxy)-9-hydroxy-deca-1,3,7-trien-5-ynyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-butyric acid methyl ester

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Chemical Property of 4-{(4S,5R)-5-[(1E,3E,7E)-(S)-10-(4-Fluoro-phenoxy)-9-hydroxy-deca-1,3,7-trien-5-ynyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-butyric acid methyl ester

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Technology Process of 4-{(4S,5R)-5-[(1E,3E,7E)-(S)-10-(4-Fluoro-phenoxy)-9-hydroxy-deca-1,3,7-trien-5-ynyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-butyric acid methyl ester

There total 16 articles about 4-{(4S,5R)-5-[(1E,3E,7E)-(S)-10-(4-Fluoro-phenoxy)-9-hydroxy-deca-1,3,7-trien-5-ynyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-butyric acid methyl ester 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: 75.0%

: 368886-33-3
4-[(4S,5R)-5-((1E,3E)-Hexa-1,3-dien-5-ynyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-butyric acid methyl ester

: 524714-06-5
(1E,3S)-1-bromo-4-(4-fluorophenoxy)-3-hydroxy-1-butene

: 620973-14-0
4-{(4S,5R)-5-[(1E,3E,7E)-(S)-10-(4-Fluoro-phenoxy)-9-hydroxy-deca-1,3,7-trien-5-ynyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-butyric acid methyl ester

Guidance literature:: With propylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; at 20 ℃;
DOI:10.1016/S0960-894X(03)00667-X

Reference yield:

: 22900-10-3,35536-75-5,36792-85-5,113890-34-9,113890-37-2,133813-23-7
2-deoxy-D-ribose

: 620973-14-0
4-{(4S,5R)-5-[(1E,3E,7E)-(S)-10-(4-Fluoro-phenoxy)-9-hydroxy-deca-1,3,7-trien-5-ynyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-butyric acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 43 percent / PPTS / ethyl acetate / 20 °C

2: 81 percent / BzOH / tetrahydrofuran / Heating

3: 87 percent / H₂ / Pd/C / ethanol

4: 86 percent / (COCl₂)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

5: 36 percent / LiNTMS₂ / toluene / -78 °C

6: 99 percent / KF; 18-crown-6 / dimethylformamide / 20 °C

7: 75 percent / Pd(PPh₃)4; CuI; nPrNH₂ / toluene / 20 °C

With propylamine; potassium fluoride; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 18-crown-6 ether; (COCl₂)2; hydrogen; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; benzyl alcohol; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; 2: Wittig reaction / 4: Swern oxidation / 5: Wadsworth-Emmons reaction;
DOI:10.1016/S0960-894X(03)00667-X

Reference yield:

: 86795-44-0,86795-47-3,147976-25-8,147976-26-9
3,4-O-isopropylidene-2-deoxy-D-ribose

: 620973-14-0
4-{(4S,5R)-5-[(1E,3E,7E)-(S)-10-(4-Fluoro-phenoxy)-9-hydroxy-deca-1,3,7-trien-5-ynyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-butyric acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 81 percent / BzOH / tetrahydrofuran / Heating

2: 87 percent / H₂ / Pd/C / ethanol

3: 86 percent / (COCl₂)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

4: 36 percent / LiNTMS₂ / toluene / -78 °C

5: 99 percent / KF; 18-crown-6 / dimethylformamide / 20 °C

6: 75 percent / Pd(PPh₃)4; CuI; nPrNH₂ / toluene / 20 °C

With propylamine; potassium fluoride; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 18-crown-6 ether; (COCl₂)2; hydrogen; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; benzyl alcohol; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Wittig reaction / 3: Swern oxidation / 4: Wadsworth-Emmons reaction;
DOI:10.1016/S0960-894X(03)00667-X