(2E,4E,14E,20E)-(7R,8R,9R,10R,13S,17R,19R,23S,24R,25S,26S)-9-(tert-Butyl-dimethyl-silanyloxy)-23,25-dihydroxy-13,19-dimethoxy-8,10,17,24,26-pentamethyl-7-methylsulfanylmethoxy-27-trityloxy-heptacosa-2,4,14,20-tetraenoic acid ethyl ester

Base Information

Chemical Name:(2E,4E,14E,20E)-(7R,8R,9R,10R,13S,17R,19R,23S,24R,25S,26S)-9-(tert-Butyl-dimethyl-silanyloxy)-23,25-dihydroxy-13,19-dimethoxy-8,10,17,24,26-pentamethyl-7-methylsulfanylmethoxy-27-trityloxy-heptacosa-2,4,14,20-tetraenoic acid ethyl ester
CAS No.:188359-34-4
Molecular Formula:C₆₃H₉₆O₉SSi
Molecular Weight:1057.6
Hs Code.:

(2E,4E,14E,20E)-(7R,8R,9R,10R,13S,17R,19R,23S,24R,25S,26S)-9-(tert-Butyl-dimethyl-silanyloxy)-23,25-dihydroxy-13,19-dimethoxy-8,10,17,24,26-pentamethyl-7-methylsulfanylmethoxy-27-trityloxy-heptacosa-2,4,14,20-tetraenoic acid ethyl ester

Synonyms:(2E,4E,14E,20E)-(7R,8R,9R,10R,13S,17R,19R,23S,24R,25S,26S)-9-(tert-Butyl-dimethyl-silanyloxy)-23,25-dihydroxy-13,19-dimethoxy-8,10,17,24,26-pentamethyl-7-methylsulfanylmethoxy-27-trityloxy-heptacosa-2,4,14,20-tetraenoic acid ethyl ester

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Chemical Property of (2E,4E,14E,20E)-(7R,8R,9R,10R,13S,17R,19R,23S,24R,25S,26S)-9-(tert-Butyl-dimethyl-silanyloxy)-23,25-dihydroxy-13,19-dimethoxy-8,10,17,24,26-pentamethyl-7-methylsulfanylmethoxy-27-trityloxy-heptacosa-2,4,14,20-tetraenoic acid ethyl ester

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Technology Process of (2E,4E,14E,20E)-(7R,8R,9R,10R,13S,17R,19R,23S,24R,25S,26S)-9-(tert-Butyl-dimethyl-silanyloxy)-23,25-dihydroxy-13,19-dimethoxy-8,10,17,24,26-pentamethyl-7-methylsulfanylmethoxy-27-trityloxy-heptacosa-2,4,14,20-tetraenoic acid ethyl ester

There total 24 articles about (2E,4E,14E,20E)-(7R,8R,9R,10R,13S,17R,19R,23S,24R,25S,26S)-9-(tert-Butyl-dimethyl-silanyloxy)-23,25-dihydroxy-13,19-dimethoxy-8,10,17,24,26-pentamethyl-7-methylsulfanylmethoxy-27-trityloxy-heptacosa-2,4,14,20-tetraenoic acid ethyl 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: 91.0%

: 423772-15-0
(2E,4E,14E,20E)-(7R,8R,9R,10R,13S,17R,19R,23S,24R,25S,26S)-9-(tert-Butyl-dimethyl-silanyloxy)-13,19-dimethoxy-8,10,17,24,26-pentamethyl-7-methylsulfanylmethoxy-23,25-bis-triethylsilanyloxy-27-trityloxy-heptacosa-2,4,14,20-tetraenoic acid ethyl ester

: 188359-34-4
(2E,4E,14E,20E)-(7R,8R,9R,10R,13S,17R,19R,23S,24R,25S,26S)-9-(tert-Butyl-dimethyl-silanyloxy)-23,25-dihydroxy-13,19-dimethoxy-8,10,17,24,26-pentamethyl-7-methylsulfanylmethoxy-27-trityloxy-heptacosa-2,4,14,20-tetraenoic acid ethyl ester

Guidance literature:: With pyridine; pyridine hydrogenfluoride; In tetrahydrofuran; at 20 ℃; for 1h;
DOI:10.1016/S0040-4020(01)01206-6

Reference yield:

: 158783-76-7
(S)-2-methyl-1-(triisopropylsilyloxy)pentan-3-one

: 188359-34-4
(2E,4E,14E,20E)-(7R,8R,9R,10R,13S,17R,19R,23S,24R,25S,26S)-9-(tert-Butyl-dimethyl-silanyloxy)-23,25-dihydroxy-13,19-dimethoxy-8,10,17,24,26-pentamethyl-7-methylsulfanylmethoxy-27-trityloxy-heptacosa-2,4,14,20-tetraenoic acid ethyl ester

Guidance literature:: Multi-step reaction with 15 steps

1: 83 percent / Sn(OTf)2; Et₃N / CH₂Cl₂ / -78 - -20 °C

2: 80 percent / Me₄NBH(OAc)3 / acetonitrile; acetic acid / 25 h / -20 °C

3: 100 percent / hydrogen / 20 percent Pd(OH)2/C / dioxane / 15 h / 20 °C

4: 93 percent / PBu₃ / dimethylformamide / 1.5 h / 20 °C

5: 100 percent / Bu₄NF / tetrahydrofuran / 3 h / 20 °C

6: 96 percent / pyridine / 11.5 h / 50 °C

7: 93 percent / imidazole / dimethylformamide / 1.5 h / 50 °C

8: 98 percent / m-chloroperbenzoic acid; NaHCO₃ / CH₂Cl₂ / 1.5 h / 20 °C

9: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

10: DMAP / pyridine / 3.5 h / 20 °C

11: 5 percent Na-Hg; NaH₂PO₄ / methanol / 35 h / 0 °C

12: 96 percent / DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

13: 83 percent / C₆H₄(COO)I(OAc)3 / CH₂Cl₂ / 0.25 h / 20 °C

14: 94 percent / LDA / tetrahydrofuran / -48 - 0 °C

15: 91 percent / HF-pyridine; pyridine / tetrahydrofuran / 1 h / 20 °C

With pyridine; 1H-imidazole; dmap; sodium dihydrogenphosphate; tin(II) trifluoromethanesulfonate; n-butyllithium; sodium amalgam; tributylphosphine; C₆H₄(COO)I(OAc)3; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; pyridine hydrogenfluoride; triethylamine; 3-chloro-benzenecarboperoxoic acid; tetramethylammonium triacetoxyborohydride; lithium diisopropyl amide; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; hexane; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4020(01)01206-6

Reference yield:

: 423772-05-8
(2S,3S,4R,5S)-7-Benzyloxy-2,4-dimethyl-1-triisopropylsilanyloxy-heptane-3,5-diol

: 188359-34-4
(2E,4E,14E,20E)-(7R,8R,9R,10R,13S,17R,19R,23S,24R,25S,26S)-9-(tert-Butyl-dimethyl-silanyloxy)-23,25-dihydroxy-13,19-dimethoxy-8,10,17,24,26-pentamethyl-7-methylsulfanylmethoxy-27-trityloxy-heptacosa-2,4,14,20-tetraenoic acid ethyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: 100 percent / hydrogen / 20 percent Pd(OH)2/C / dioxane / 15 h / 20 °C

2: 93 percent / PBu₃ / dimethylformamide / 1.5 h / 20 °C

3: 100 percent / Bu₄NF / tetrahydrofuran / 3 h / 20 °C

4: 96 percent / pyridine / 11.5 h / 50 °C

5: 93 percent / imidazole / dimethylformamide / 1.5 h / 50 °C

6: 98 percent / m-chloroperbenzoic acid; NaHCO₃ / CH₂Cl₂ / 1.5 h / 20 °C

7: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

8: DMAP / pyridine / 3.5 h / 20 °C

9: 5 percent Na-Hg; NaH₂PO₄ / methanol / 35 h / 0 °C

10: 96 percent / DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

11: 83 percent / C₆H₄(COO)I(OAc)3 / CH₂Cl₂ / 0.25 h / 20 °C

12: 94 percent / LDA / tetrahydrofuran / -48 - 0 °C

13: 91 percent / HF-pyridine; pyridine / tetrahydrofuran / 1 h / 20 °C

With pyridine; 1H-imidazole; dmap; sodium dihydrogenphosphate; n-butyllithium; sodium amalgam; tributylphosphine; C₆H₄(COO)I(OAc)3; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; pyridine hydrogenfluoride; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)01206-6