(2E,4Z,6S,7R,8E,10S,11R,12S,14S,15R)-15-(3-Amino-2,5-dimethoxyphenyl)-7-(tert-butyldimethylsiloxy)-11,12,15-trimethoxy-2,6,8,10,14-pentamethyl-2,4,8-pentadecatrienoic acid

Base Information

Chemical Name:(2E,4Z,6S,7R,8E,10S,11R,12S,14S,15R)-15-(3-Amino-2,5-dimethoxyphenyl)-7-(tert-butyldimethylsiloxy)-11,12,15-trimethoxy-2,6,8,10,14-pentamethyl-2,4,8-pentadecatrienoic acid
CAS No.:123083-98-7
Molecular Formula:C₃₇H₆₃NO₈Si
Molecular Weight:677.995
Hs Code.:

(2E,4Z,6S,7R,8E,10S,11R,12S,14S,15R)-15-(3-Amino-2,5-dimethoxyphenyl)-7-(tert-butyldimethylsiloxy)-11,12,15-trimethoxy-2,6,8,10,14-pentamethyl-2,4,8-pentadecatrienoic acid

Synonyms:(2E,4Z,6S,7R,8E,10S,11R,12S,14S,15R)-15-(3-Amino-2,5-dimethoxyphenyl)-7-(tert-butyldimethylsiloxy)-11,12,15-trimethoxy-2,6,8,10,14-pentamethyl-2,4,8-pentadecatrienoic acid

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Chemical Property of (2E,4Z,6S,7R,8E,10S,11R,12S,14S,15R)-15-(3-Amino-2,5-dimethoxyphenyl)-7-(tert-butyldimethylsiloxy)-11,12,15-trimethoxy-2,6,8,10,14-pentamethyl-2,4,8-pentadecatrienoic acid

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Technology Process of (2E,4Z,6S,7R,8E,10S,11R,12S,14S,15R)-15-(3-Amino-2,5-dimethoxyphenyl)-7-(tert-butyldimethylsiloxy)-11,12,15-trimethoxy-2,6,8,10,14-pentamethyl-2,4,8-pentadecatrienoic acid

There total 50 articles about (2E,4Z,6S,7R,8E,10S,11R,12S,14S,15R)-15-(3-Amino-2,5-dimethoxyphenyl)-7-(tert-butyldimethylsiloxy)-11,12,15-trimethoxy-2,6,8,10,14-pentamethyl-2,4,8-pentadecatrienoic 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: 100.0%

: 138694-29-8
Methyl (2E,4Z,6S,7R,8E,10S,11R,12S,14S,15R)-15-(3-amino-2,5-dimethoxyphenyl)-7-(tert-butyldimethylsiloxy)-11,12,15-trimethoxy-2,6,8,10,14-pentamethyl-2,4,8-pentadecatrienoate

: 123083-98-7
(2E,4Z,6S,7R,8E,10S,11R,12S,14S,15R)-15-(3-Amino-2,5-dimethoxyphenyl)-7-(tert-butyldimethylsiloxy)-11,12,15-trimethoxy-2,6,8,10,14-pentamethyl-2,4,8-pentadecatrienoic acid

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; methanol; water;
DOI:10.1021/jo00030a006

Reference yield:

: 99968-60-2,27652-16-0
methyl (E)-4-bromo-2-methylbut-2-enoate

: 123083-98-7
(2E,4Z,6S,7R,8E,10S,11R,12S,14S,15R)-15-(3-Amino-2,5-dimethoxyphenyl)-7-(tert-butyldimethylsiloxy)-11,12,15-trimethoxy-2,6,8,10,14-pentamethyl-2,4,8-pentadecatrienoic acid

Guidance literature:: Multi-step reaction with 6 steps

1: 73 percent / 1 h / 110 °C

2: PCl₅ / 1) 2 h, r.t., 2) 6 h, 75 deg C

3: Huenig's base / benzene / 1) 30 min, 0 deg C, 2) 13 h, r.t.

4: 1) n-BuLi / 1) Et₂O, a) -78 deg C, 15 min, b) -20 deg C, 15 min 2) Et₂O, -78 deg C to -60 deg C, 4 h

5: 94 percent / H₂, quinoline / Lindlar's catalyst / ethanol / 10.5 h

6: 99 percent / LiOH / methanol; tetrahydrofuran; H₂O / 32 h / Ambient temperature

With quinoline; lithium hydroxide; n-butyllithium; phosphorus pentachloride; hydrogen; N-ethyl-N,N-diisopropylamine; Lindlar's catalyst; In tetrahydrofuran; methanol; ethanol; water; benzene;
DOI:10.1021/jo00054a035

Reference yield:

: 138694-33-4
(2E,4S,5R,6E)-5-Methoxy-2,4-dimethyl-7-phenyl-2,6-heptadien-1-al

: 123083-98-7
(2E,4Z,6S,7R,8E,10S,11R,12S,14S,15R)-15-(3-Amino-2,5-dimethoxyphenyl)-7-(tert-butyldimethylsiloxy)-11,12,15-trimethoxy-2,6,8,10,14-pentamethyl-2,4,8-pentadecatrienoic acid

Guidance literature:: Multi-step reaction with 13 steps

2: 1) Me₃Al / 1) CH₂Cl₂, toluene, 30 min, r.t., 2) CH₂Cl₂, 18 h, -20 deg C

3: 91 percent / imidazole / dimethylformamide / 18 h / Ambient temperature

4: 1) OsO₄, N-methylmorpholine oxide, 2) NaIO₄, NaHCO₃ / 1) t-BuOH, water, THF, 3 h, r.t., 2) water, 45 min

5: 1) TiCl₄, Et₃N / 1) CH₂Cl₂, 1 h, 0 deg C, 2) CH₂Cl₂, 0 deg C, 3.3 h

6: 81 percent / Dess-Martin periodinane, pyridine / CH₂Cl₂ / 0.5 h / Ambient temperature

7: 70 percent / LiOH / tetrahydrofuran; H₂O / 1) 5 min, 0 deg C, 2) 3 h, r.t.

8: 98 percent / Zn(BH₄)2, cyclohexene / CH₂Cl₂ / 1) -78 deg C, 30 min, 2) -45 deg C, 1 h, 3) -15 deg C, 1 h

9: 86 percent / Proton Sponge / CH₂Cl₂ / 3 h / Ambient temperature

10: 95 percent / DIBAL / tetrahydrofuran; toluene / 0.75 h / -78 °C

11: 1) n-BuLi / 1) Et₂O, a) -78 deg C, 15 min, b) -20 deg C, 15 min 2) Et₂O, -78 deg C to -60 deg C, 4 h

12: 94 percent / H₂, quinoline / Lindlar's catalyst / ethanol / 10.5 h

13: 99 percent / LiOH / methanol; tetrahydrofuran; H₂O / 32 h / Ambient temperature

With pyridine; 1H-imidazole; quinoline; lithium hydroxide; sodium periodate; osmium(VIII) oxide; n-butyllithium; zinc(II) tetrahydroborate; Proton Sponge; hydrogen; trimethylaluminum; titanium tetrachloride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; 4-methylmorpholine N-oxide; triethylamine; cyclohexene; Lindlar's catalyst; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00054a035