Benzoic acid (5E,12E)-(1R,3S,9R,10R)-3-(tert-butyl-dimethyl-silanyloxy)-1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-14-hydroxy-9-(4-methoxy-benzyloxy)-10-methyl-tetradeca-5,12-dien-7-ynyl ester

Base Information

Chemical Name:Benzoic acid (5E,12E)-(1R,3S,9R,10R)-3-(tert-butyl-dimethyl-silanyloxy)-1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-14-hydroxy-9-(4-methoxy-benzyloxy)-10-methyl-tetradeca-5,12-dien-7-ynyl ester
CAS No.:775307-33-0
Molecular Formula:C₅₄H₇₂O₇Si₂
Molecular Weight:889.332
Hs Code.:

Benzoic acid (5E,12E)-(1R,3S,9R,10R)-3-(tert-butyl-dimethyl-silanyloxy)-1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-14-hydroxy-9-(4-methoxy-benzyloxy)-10-methyl-tetradeca-5,12-dien-7-ynyl ester

Synonyms:Benzoic acid (5E,12E)-(1R,3S,9R,10R)-3-(tert-butyl-dimethyl-silanyloxy)-1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-14-hydroxy-9-(4-methoxy-benzyloxy)-10-methyl-tetradeca-5,12-dien-7-ynyl ester

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Chemical Property of Benzoic acid (5E,12E)-(1R,3S,9R,10R)-3-(tert-butyl-dimethyl-silanyloxy)-1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-14-hydroxy-9-(4-methoxy-benzyloxy)-10-methyl-tetradeca-5,12-dien-7-ynyl ester

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Technology Process of Benzoic acid (5E,12E)-(1R,3S,9R,10R)-3-(tert-butyl-dimethyl-silanyloxy)-1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-14-hydroxy-9-(4-methoxy-benzyloxy)-10-methyl-tetradeca-5,12-dien-7-ynyl ester

There total 20 articles about Benzoic acid (5E,12E)-(1R,3S,9R,10R)-3-(tert-butyl-dimethyl-silanyloxy)-1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-14-hydroxy-9-(4-methoxy-benzyloxy)-10-methyl-tetradeca-5,12-dien-7-ynyl 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: 87.0%

: 775307-31-8
benzoic acid 3-(tert-butyl-dimethyl-silanyloxy)-1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-6-iodo-hex-5-enyl ester

: 397886-47-4
(E)-(5R,6R)-6-(4-Methoxy-benzyloxy)-5-methyl-oct-2-en-7-yn-1-ol

: 775307-33-0
Benzoic acid (5E,12E)-(1R,3S,9R,10R)-3-(tert-butyl-dimethyl-silanyloxy)-1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-14-hydroxy-9-(4-methoxy-benzyloxy)-10-methyl-tetradeca-5,12-dien-7-ynyl ester

Guidance literature:: With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; at 20 ℃; for 2h;
DOI:10.1021/jo049084a

Reference yield:

: 775306-99-5
(R)-2-[(R)-2-(2-Methoxy-ethoxymethoxy)-pent-4-enyl]-oxirane

: 775307-33-0
Benzoic acid (5E,12E)-(1R,3S,9R,10R)-3-(tert-butyl-dimethyl-silanyloxy)-1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-14-hydroxy-9-(4-methoxy-benzyloxy)-10-methyl-tetradeca-5,12-dien-7-ynyl ester

Guidance literature:: Multi-step reaction with 14 steps

1.1: 90 percent / tetrahydrofuran; hexane / 1.5 h / -78 °C

2.1: 94 percent / TBAF / tetrahydrofuran / 1 h / 0 °C

3.1: 100 percent / imidazole; DMAP / CH₂Cl₂

4.1: 94 percent / carbon tetrabromide; i-PrOH / 12 h / Heating

5.1: 95 percent / pyridine / CH₂Cl₂

6.1: 96 percent / HF*pyridine / pyridine; tetrahydrofuran / 144 h / 20 °C

7.1: camphorsulfonic acid / CH₂Cl₂ / 0 - 20 °C

8.1: ozone / methanol / -78 °C

9.1: sodium borohydride / methanol / -78 °C

10.1: 100 percent / ammonium nitrate / dimethylformamide

11.1: 91 percent / DDQ / CH₂Cl₂; H₂O / 1 h

12.1: 96 percent / imidazole; DMAP / CH₂Cl₂

13.1: (n-Bu)3SnH; AIBN / benzene / 3.5 h / Heating

13.2: 94 percent / iodine / CH₂Cl₂ / 0.17 h / 0 °C

14.1: 87 percent / triethylamine / Pd(PPh₃)2Cl₂; CuI / 2 h / 20 °C

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; ammonium nitrate; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; pyridine hydrogenfluoride; ozone; triethylamine; isopropyl alcohol; 2,3-dicyano-5,6-dichloro-p-benzoquinone; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; benzene; 14.1: Sonogashira coupling;
DOI:10.1021/jo049084a

Reference yield:

: 775307-53-4
(S)-4-[(R)-2-(2-Methoxy-ethoxymethoxy)-pent-4-enyl]-2,2-dimethyl-[1,3]dioxolane

: 775307-33-0
Benzoic acid (5E,12E)-(1R,3S,9R,10R)-3-(tert-butyl-dimethyl-silanyloxy)-1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-14-hydroxy-9-(4-methoxy-benzyloxy)-10-methyl-tetradeca-5,12-dien-7-ynyl ester

Guidance literature:: Multi-step reaction with 18 steps

1.1: 84 percent / acetic acid; water / tetrahydrofuran / 12 h / 50 °C

2.1: 100 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

3.1: 100 percent / DMAP; pyridine / CH₂Cl₂ / 0 - 20 °C

4.1: 98 percent / K₂CO₃ / methanol / 20 °C

5.1: 90 percent / tetrahydrofuran; hexane / 1.5 h / -78 °C

6.1: 94 percent / TBAF / tetrahydrofuran / 1 h / 0 °C

7.1: 100 percent / imidazole; DMAP / CH₂Cl₂

8.1: 94 percent / carbon tetrabromide; i-PrOH / 12 h / Heating

9.1: 95 percent / pyridine / CH₂Cl₂

10.1: 96 percent / HF*pyridine / pyridine; tetrahydrofuran / 144 h / 20 °C

11.1: camphorsulfonic acid / CH₂Cl₂ / 0 - 20 °C

12.1: ozone / methanol / -78 °C

13.1: sodium borohydride / methanol / -78 °C

14.1: 100 percent / ammonium nitrate / dimethylformamide

15.1: 91 percent / DDQ / CH₂Cl₂; H₂O / 1 h

16.1: 96 percent / imidazole; DMAP / CH₂Cl₂

17.1: (n-Bu)3SnH; AIBN / benzene / 3.5 h / Heating

17.2: 94 percent / iodine / CH₂Cl₂ / 0.17 h / 0 °C

18.1: 87 percent / triethylamine / Pd(PPh₃)2Cl₂; CuI / 2 h / 20 °C

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; ammonium nitrate; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; water; tri-n-butyl-tin hydride; potassium carbonate; pyridine hydrogenfluoride; ozone; acetic acid; triethylamine; isopropyl alcohol; 2,3-dicyano-5,6-dichloro-p-benzoquinone; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; benzene; 18.1: Sonogashira coupling;
DOI:10.1021/jo049084a