phenoxy-acetic acid 1-{5-(2-allyloxycarbonylamino-ethyl)-2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-5-[2-(3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-vinyl]-[1,3]dioxolan-4-ylmethyl}-5-[3-(4-methoxy-phenoxymethoxy)-cyclohexyl]-penta-2,4-dienyl ester

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Chemical Name:phenoxy-acetic acid 1-{5-(2-allyloxycarbonylamino-ethyl)-2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-5-[2-(3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-vinyl]-[1,3]dioxolan-4-ylmethyl}-5-[3-(4-methoxy-phenoxymethoxy)-cyclohexyl]-penta-2,4-dienyl ester
CAS No.:521274-35-1
Molecular Formula:C₅₈H₇₅NO₁₃Si
Molecular Weight:1022.32
Hs Code.:

phenoxy-acetic acid 1-{5-(2-allyloxycarbonylamino-ethyl)-2-[4-(<i>tert</i>-butyl-dimethyl-silanyloxy)-phenyl]-5-[2-(3-ethyl-6-oxo-3,6-dihydro-2<i>H</i>-pyran-2-yl)-vinyl]-[1,3]dioxolan-4-ylmethyl}-5-[3-(4-methoxy-phenoxymethoxy)-cyclohexyl]-penta-2,4-dienyl ester

Synonyms:phenoxy-acetic acid 1-{5-(2-allyloxycarbonylamino-ethyl)-2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-5-[2-(3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-vinyl]-[1,3]dioxolan-4-ylmethyl}-5-[3-(4-methoxy-phenoxymethoxy)-cyclohexyl]-penta-2,4-dienyl ester

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Chemical Property of phenoxy-acetic acid 1-{5-(2-allyloxycarbonylamino-ethyl)-2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-5-[2-(3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-vinyl]-[1,3]dioxolan-4-ylmethyl}-5-[3-(4-methoxy-phenoxymethoxy)-cyclohexyl]-penta-2,4-dienyl ester

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Technology Process of phenoxy-acetic acid 1-{5-(2-allyloxycarbonylamino-ethyl)-2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-5-[2-(3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-vinyl]-[1,3]dioxolan-4-ylmethyl}-5-[3-(4-methoxy-phenoxymethoxy)-cyclohexyl]-penta-2,4-dienyl ester

There total 33 articles about phenoxy-acetic acid 1-{5-(2-allyloxycarbonylamino-ethyl)-2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-5-[2-(3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-vinyl]-[1,3]dioxolan-4-ylmethyl}-5-[3-(4-methoxy-phenoxymethoxy)-cyclohexyl]-penta-2,4-dienyl 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:

: 120743-99-9
p-[(tert-butyldimethylsilyl)oxy]benzaldehyde

: 521274-35-1
phenoxy-acetic acid 1-{5-(2-allyloxycarbonylamino-ethyl)-2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-5-[2-(3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-vinyl]-[1,3]dioxolan-4-ylmethyl}-5-[3-(4-methoxy-phenoxymethoxy)-cyclohexyl]-penta-2,4-dienyl ester

Guidance literature:: Multi-step reaction with 21 steps

1.1: 6.82 g / CSA / methanol / 20 h / 23 °C

2.1: CSA / dimethylformamide / 0.67 h / 50 °C

3.1: 4.67 g / TBAF / tetrahydrofuran / 1.5 h / 20 °C

4.1: MnO₂ / CH₂Cl₂ / 3 h / 20 °C

5.1: 2.51 g / imidazole / CH₂Cl₂ / 1 h / 20 °C

6.1: n-Bu₂BOTf; i-Pr₂NEt / CH₂Cl₂ / 0.67 h / 0 °C

6.2: CH₂Cl₂ / 5 h / -78 - 20 °C

7.1: imidazole / dimethylformamide / 0.08 h / 20 °C

8.1: 1.02 g / tetrahydrofuran; hexane / 1.5 h / 0 °C

9.1: DIBAL / toluene / -78 °C

10.1: (n-Bu)4N⁽¹⁺⁾*OH^(1-) / tetrahydrofuran; methanol / 3.5 h / -78 - -18 °C

11.1: PPTS / methanol; tetrahydrofuran / 1 h / 20 °C

12.1: 99 percent / Ti(Oi-Pr)4 / benzene / 0.25 h / 80 °C

13.1: 62 percent / K₂OsO₄*2H₂O; (DHQD)2PHAL; K₃Fe(CN)6 / NaHCO₃ / 2-methyl-propan-2-ol; H₂O / 96 h / 20 °C

14.1: Pb(OAc)4; K₂CO₃ / benzene / 0.08 h / 20 °C

15.1: 400 mg / toluene; diethyl ether; hexane / 3 h / -78 - -10 °C

16.1: Zn; LiCuBr₂ / ethanol / 0.33 h / 80 °C

17.1: 364 mg / pyridine / CH₂Cl₂ / 0.33 h / 0 °C

18.1: ZnBr₂; Et₃SiH / CH₂Cl₂ / 2 h / -18 °C

18.2: 68 percent / PPTS / methanol; tetrahydrofuran / 0.17 h / 20 °C

19.1: 73 percent / HN₃; PPh₃; DEAD / toluene / 0.17 h / 0 °C

20.1: PPh₃; water / tetrahydrofuran / 22 h / 20 °C

21.1: 48.5 mg / pyridine / tetrahydrofuran / 0.17 h / 20 °C

With pyridine; 1H-imidazole; lead(IV) acetate; titanium(IV) isopropylate; triethylsilane; manganese(IV) oxide; potassium osmate(VI); tris-(2-chloro-ethyl)-amine; Br₂Cu^(1-)*Li⁽¹⁺⁾; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydroxide; water; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; zinc dibromide; potassium hexacyanoferrate(III); zinc; diethylazodicarboxylate; sodium hydrogencarbonate; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; benzene;
DOI:10.1021/ja0340679

Reference yield:

: 123-08-0,65581-83-1
4-hydroxy-benzaldehyde

: 521274-35-1
phenoxy-acetic acid 1-{5-(2-allyloxycarbonylamino-ethyl)-2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-5-[2-(3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-vinyl]-[1,3]dioxolan-4-ylmethyl}-5-[3-(4-methoxy-phenoxymethoxy)-cyclohexyl]-penta-2,4-dienyl ester

Guidance literature:: Multi-step reaction with 22 steps

1.1: imidazole / CH₂Cl₂ / 0.5 h / 23 °C

2.1: 6.82 g / CSA / methanol / 20 h / 23 °C

3.1: CSA / dimethylformamide / 0.67 h / 50 °C

4.1: 4.67 g / TBAF / tetrahydrofuran / 1.5 h / 20 °C

5.1: MnO₂ / CH₂Cl₂ / 3 h / 20 °C

6.1: 2.51 g / imidazole / CH₂Cl₂ / 1 h / 20 °C

7.1: n-Bu₂BOTf; i-Pr₂NEt / CH₂Cl₂ / 0.67 h / 0 °C

7.2: CH₂Cl₂ / 5 h / -78 - 20 °C

8.1: imidazole / dimethylformamide / 0.08 h / 20 °C

9.1: 1.02 g / tetrahydrofuran; hexane / 1.5 h / 0 °C

10.1: DIBAL / toluene / -78 °C

11.1: (n-Bu)4N⁽¹⁺⁾*OH^(1-) / tetrahydrofuran; methanol / 3.5 h / -78 - -18 °C

12.1: PPTS / methanol; tetrahydrofuran / 1 h / 20 °C

13.1: 99 percent / Ti(Oi-Pr)4 / benzene / 0.25 h / 80 °C

14.1: 62 percent / K₂OsO₄*2H₂O; (DHQD)2PHAL; K₃Fe(CN)6 / NaHCO₃ / 2-methyl-propan-2-ol; H₂O / 96 h / 20 °C

15.1: Pb(OAc)4; K₂CO₃ / benzene / 0.08 h / 20 °C

16.1: 400 mg / toluene; diethyl ether; hexane / 3 h / -78 - -10 °C

17.1: Zn; LiCuBr₂ / ethanol / 0.33 h / 80 °C

18.1: 364 mg / pyridine / CH₂Cl₂ / 0.33 h / 0 °C

19.1: ZnBr₂; Et₃SiH / CH₂Cl₂ / 2 h / -18 °C

19.2: 68 percent / PPTS / methanol; tetrahydrofuran / 0.17 h / 20 °C

20.1: 73 percent / HN₃; PPh₃; DEAD / toluene / 0.17 h / 0 °C

21.1: PPh₃; water / tetrahydrofuran / 22 h / 20 °C

22.1: 48.5 mg / pyridine / tetrahydrofuran / 0.17 h / 20 °C

With pyridine; 1H-imidazole; lead(IV) acetate; titanium(IV) isopropylate; triethylsilane; manganese(IV) oxide; potassium osmate(VI); tris-(2-chloro-ethyl)-amine; Br₂Cu^(1-)*Li⁽¹⁺⁾; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydroxide; water; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; zinc dibromide; potassium hexacyanoferrate(III); zinc; diethylazodicarboxylate; sodium hydrogencarbonate; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; benzene;
DOI:10.1021/ja0340679

Reference yield:

: 118736-04-2
(4-(dimethoxymethyl)phenoxy)(tert-butyl)dimethylsilane

: 521274-35-1
phenoxy-acetic acid 1-{5-(2-allyloxycarbonylamino-ethyl)-2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-5-[2-(3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-vinyl]-[1,3]dioxolan-4-ylmethyl}-5-[3-(4-methoxy-phenoxymethoxy)-cyclohexyl]-penta-2,4-dienyl ester

Guidance literature:: Multi-step reaction with 20 steps

1.1: CSA / dimethylformamide / 0.67 h / 50 °C

2.1: 4.67 g / TBAF / tetrahydrofuran / 1.5 h / 20 °C

3.1: MnO₂ / CH₂Cl₂ / 3 h / 20 °C

4.1: 2.51 g / imidazole / CH₂Cl₂ / 1 h / 20 °C

5.1: n-Bu₂BOTf; i-Pr₂NEt / CH₂Cl₂ / 0.67 h / 0 °C

5.2: CH₂Cl₂ / 5 h / -78 - 20 °C

6.1: imidazole / dimethylformamide / 0.08 h / 20 °C

7.1: 1.02 g / tetrahydrofuran; hexane / 1.5 h / 0 °C

8.1: DIBAL / toluene / -78 °C

9.1: (n-Bu)4N⁽¹⁺⁾*OH^(1-) / tetrahydrofuran; methanol / 3.5 h / -78 - -18 °C

10.1: PPTS / methanol; tetrahydrofuran / 1 h / 20 °C

11.1: 99 percent / Ti(Oi-Pr)4 / benzene / 0.25 h / 80 °C

12.1: 62 percent / K₂OsO₄*2H₂O; (DHQD)2PHAL; K₃Fe(CN)6 / NaHCO₃ / 2-methyl-propan-2-ol; H₂O / 96 h / 20 °C

13.1: Pb(OAc)4; K₂CO₃ / benzene / 0.08 h / 20 °C

14.1: 400 mg / toluene; diethyl ether; hexane / 3 h / -78 - -10 °C

15.1: Zn; LiCuBr₂ / ethanol / 0.33 h / 80 °C

16.1: 364 mg / pyridine / CH₂Cl₂ / 0.33 h / 0 °C

17.1: ZnBr₂; Et₃SiH / CH₂Cl₂ / 2 h / -18 °C

17.2: 68 percent / PPTS / methanol; tetrahydrofuran / 0.17 h / 20 °C

18.1: 73 percent / HN₃; PPh₃; DEAD / toluene / 0.17 h / 0 °C

19.1: PPh₃; water / tetrahydrofuran / 22 h / 20 °C

20.1: 48.5 mg / pyridine / tetrahydrofuran / 0.17 h / 20 °C

With pyridine; 1H-imidazole; lead(IV) acetate; titanium(IV) isopropylate; triethylsilane; manganese(IV) oxide; potassium osmate(VI); tris-(2-chloro-ethyl)-amine; Br₂Cu^(1-)*Li⁽¹⁺⁾; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydroxide; water; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; zinc dibromide; potassium hexacyanoferrate(III); zinc; diethylazodicarboxylate; sodium hydrogencarbonate; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; benzene;
DOI:10.1021/ja0340679