2,4,8-Pentadecatrienoic acid, 15-[3-[bis[(1,1-dimethylethoxy)carbonyl]amino]-2,5-dimethoxyphenyl]-7- hydroxy-6,11,12,15-tetramethoxy-2,8,10,14-tetramethyl-, ethyl ester, (2E,4Z,6S,7S,8E,10S,11R,12S,14S,15R)-

Base Information

Chemical Name:2,4,8-Pentadecatrienoic acid, 15-[3-[bis[(1,1-dimethylethoxy)carbonyl]amino]-2,5-dimethoxyphenyl]-7- hydroxy-6,11,12,15-tetramethoxy-2,8,10,14-tetramethyl-, ethyl ester, (2E,4Z,6S,7S,8E,10S,11R,12S,14S,15R)-
CAS No.:922166-91-4
Molecular Formula:C43H69NO13
Molecular Weight:808.02
Hs Code.:

2,4,8-Pentadecatrienoic acid,
15-[3-[bis[(1,1-dimethylethoxy)carbonyl]amino]-2,5-dimethoxyphenyl]-7-
hydroxy-6,11,12,15-tetramethoxy-2,8,10,14-tetramethyl-, ethyl ester,
(2E,4Z,6S,7S,8E,10S,11R,12S,14S,15R)-

Synonyms:

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Chemical Property of 2,4,8-Pentadecatrienoic acid, 15-[3-[bis[(1,1-dimethylethoxy)carbonyl]amino]-2,5-dimethoxyphenyl]-7- hydroxy-6,11,12,15-tetramethoxy-2,8,10,14-tetramethyl-, ethyl ester, (2E,4Z,6S,7S,8E,10S,11R,12S,14S,15R)-

Chemical Property:

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Hazard Codes:

MSDS Files:: SDS file from LookChem

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Technology Process of 2,4,8-Pentadecatrienoic acid, 15-[3-[bis[(1,1-dimethylethoxy)carbonyl]amino]-2,5-dimethoxyphenyl]-7- hydroxy-6,11,12,15-tetramethoxy-2,8,10,14-tetramethyl-, ethyl ester, (2E,4Z,6S,7S,8E,10S,11R,12S,14S,15R)-

There total 29 articles about 2,4,8-Pentadecatrienoic acid, 15-[3-[bis[(1,1-dimethylethoxy)carbonyl]amino]-2,5-dimethoxyphenyl]-7- hydroxy-6,11,12,15-tetramethoxy-2,8,10,14-tetramethyl-, ethyl ester, (2E,4Z,6S,7S,8E,10S,11R,12S,14S,15R)- 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:

: 922166-82-3
N,N-diallyl-3-bromo-2,5-dimethoxyaniline

: 922166-91-4
ethyl (2E,4Z,6S,7S,8E,10S,11R,12S,14S,15R)-15-[3-bis(tert-butoxycarbonyl)amino-2,5-dimethoxyphenyl]-7-hydroxy-6,11,12,15-tetramethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-trienoate

Guidance literature:: Multi-step reaction with 9 steps

1: 54 percent / n-BuLi / diethyl ether; hexane / 1.5 h / -78 °C

2: 100 percent / NaH / dimethylformamide / 0 - 20 °C

3: 97 percent / N,N-dimethylbarbituric acid; Pd(PPh₃)4 / CH₂Cl₂ / 2.5 h / Heating

4: 75 percent / Et₃N; N,N-dimethylaminopyridine / tetrahydrofuran / 6 h / Heating

5: TBAF / tetrahydrofuran / 24 h / 20 °C

6: 89 percent / diisopropylethylamine / CH₂Cl₂ / 6 h / -78 °C

7: 72 percent / second generation Grubbs catalyst / toluene / 2 h / Heating

8: DIBAL-H / diethyl ether; hexane / 2 h / -78 °C

9: 52.9 mg / toluene / 3.5 h / Heating

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; 1,3-dimethylbarbituric acid; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 9: Wittig reaction;
DOI:10.1021/ol062642i

Reference yield:

: tert-butyl-(4-methoxy-2-methyl-but-3-enyloxy)-diphenyl-silane

: 922166-91-4
ethyl (2E,4Z,6S,7S,8E,10S,11R,12S,14S,15R)-15-[3-bis(tert-butoxycarbonyl)amino-2,5-dimethoxyphenyl]-7-hydroxy-6,11,12,15-tetramethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-trienoate

Guidance literature:: Multi-step reaction with 24 steps

1.1: 4.37 mg / aq. HCl / tetrahydrofuran; CH₂Cl₂ / 3 h / 20 °C

2.1: 96 percent / (S,S)-chiral titanium complex / diethyl ether; tetrahydrofuran / 5 h / -78 °C

3.1: 97 percent / KH / tetrahydrofuran / 0 - 20 °C

4.1: 98 percent / [1,3-Mes₂-(N₂C₃H₅)]Cl₂(PCy₃)Ru=CHPh; N-allyl-N-tritylamine; diisopropylethylamine / toluene / 3.5 h / Heating

5.1: OsO₄; H₂O; N-methylmorpholine N-oxide / acetone / 16 h / 20 °C

6.1: aq. NaIO₄ / acetone / 2.5 h / 20 °C

7.1: 2.73 g / 4 Angstroem molecular sieves / toluene / 2.5 h / -78 - 0 °C

8.1: 92 percent / KH / tetrahydrofuran / 0 - 20 °C

9.1: OsO₄; H₂O; N-methylmorpholine N-oxide / acetone / 18 h / 20 °C

10.1: aq. NaIO₄ / acetone / 2.5 h / 20 °C

11.1: s-BuLi / tetrahydrofuran; cyclohexane / 4.5 h / -78 - -20 °C

11.2: 1.18 g / citric acid / tetrahydrofuran; cyclohexane; H₂O / pH 4 - 5

12.1: BF₃*Et₂O / tetrahydrofuran; cyclohexane / -78 - -5 °C

12.2: 1.49 g / ethanolamine / pentane / 2.5 h / 0 °C

13.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 10 h / -78 °C

14.1: 82 percent / NH₄F; MeOH / 9.5 h / Heating

15.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 4 h

16.1: 54 percent / n-BuLi / diethyl ether; hexane / 1.5 h / -78 °C

17.1: 100 percent / NaH / dimethylformamide / 0 - 20 °C

18.1: 97 percent / N,N-dimethylbarbituric acid; Pd(PPh₃)4 / CH₂Cl₂ / 2.5 h / Heating

19.1: 75 percent / Et₃N; N,N-dimethylaminopyridine / tetrahydrofuran / 6 h / Heating

20.1: TBAF / tetrahydrofuran / 24 h / 20 °C

21.1: 89 percent / diisopropylethylamine / CH₂Cl₂ / 6 h / -78 °C

22.1: 72 percent / second generation Grubbs catalyst / toluene / 2 h / Heating

23.1: DIBAL-H / diethyl ether; hexane / 2 h / -78 °C

24.1: 52.9 mg / toluene / 3.5 h / Heating

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2,6-dimethylpyridine; hydrogenchloride; methanol; dmap; ammonium fluoride; sodium periodate; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; 1,3-dimethylbarbituric acid; (S,S)-chiral titanium; [1,3-Mes₂-(N₂C₃H₅)]Cl₂(PCy₃)Ru=CHPh; 4 A molecular sieve; boron trifluoride diethyl etherate; N-tritylprop-2-en-1-amine; tetrabutyl ammonium fluoride; water; sec.-butyllithium; potassium hydride; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; cyclohexane; N,N-dimethyl-formamide; acetone; toluene; 11.1: Corey-Schlessinger olefination / 15.1: Dess-Martin oxidation / 24.1: Wittig reaction;
DOI:10.1021/ol062642i

Reference yield:

: 922166-78-7
(4R,6S)-7-tert-butyldiphenylsilyloxy-4-methoxy-6-methylhept-2-ene

: 922166-91-4
ethyl (2E,4Z,6S,7S,8E,10S,11R,12S,14S,15R)-15-[3-bis(tert-butoxycarbonyl)amino-2,5-dimethoxyphenyl]-7-hydroxy-6,11,12,15-tetramethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-trienoate

Guidance literature:: Multi-step reaction with 20 steps

1.1: OsO₄; H₂O; N-methylmorpholine N-oxide / acetone / 16 h / 20 °C

2.1: aq. NaIO₄ / acetone / 2.5 h / 20 °C

3.1: 2.73 g / 4 Angstroem molecular sieves / toluene / 2.5 h / -78 - 0 °C

4.1: 92 percent / KH / tetrahydrofuran / 0 - 20 °C

5.1: OsO₄; H₂O; N-methylmorpholine N-oxide / acetone / 18 h / 20 °C

6.1: aq. NaIO₄ / acetone / 2.5 h / 20 °C

7.1: s-BuLi / tetrahydrofuran; cyclohexane / 4.5 h / -78 - -20 °C

7.2: 1.18 g / citric acid / tetrahydrofuran; cyclohexane; H₂O / pH 4 - 5

8.1: BF₃*Et₂O / tetrahydrofuran; cyclohexane / -78 - -5 °C

8.2: 1.49 g / ethanolamine / pentane / 2.5 h / 0 °C

9.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 10 h / -78 °C

10.1: 82 percent / NH₄F; MeOH / 9.5 h / Heating

11.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 4 h

12.1: 54 percent / n-BuLi / diethyl ether; hexane / 1.5 h / -78 °C

13.1: 100 percent / NaH / dimethylformamide / 0 - 20 °C

14.1: 97 percent / N,N-dimethylbarbituric acid; Pd(PPh₃)4 / CH₂Cl₂ / 2.5 h / Heating

15.1: 75 percent / Et₃N; N,N-dimethylaminopyridine / tetrahydrofuran / 6 h / Heating

16.1: TBAF / tetrahydrofuran / 24 h / 20 °C

17.1: 89 percent / diisopropylethylamine / CH₂Cl₂ / 6 h / -78 °C

18.1: 72 percent / second generation Grubbs catalyst / toluene / 2 h / Heating

19.1: DIBAL-H / diethyl ether; hexane / 2 h / -78 °C

20.1: 52.9 mg / toluene / 3.5 h / Heating

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2,6-dimethylpyridine; methanol; dmap; ammonium fluoride; sodium periodate; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; 1,3-dimethylbarbituric acid; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; sec.-butyllithium; potassium hydride; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; cyclohexane; N,N-dimethyl-formamide; acetone; toluene; 7.1: Corey-Schlessinger olefination / 11.1: Dess-Martin oxidation / 20.1: Wittig reaction;
DOI:10.1021/ol062642i