(2R,3R,4E,6S,7R,8S,10S,11R)-<(tert-Butyldimethylsilyl)oxy>-11-(2,5-dimethoxy-3-nitrophenyl)-8-hydroxy-N,7,8,11-tetramethoxy-N,2,4,6,10-pentamethyl-4-undecenal

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Chemical Name:(2R,3R,4E,6S,7R,8S,10S,11R)-<(tert-Butyldimethylsilyl)oxy>-11-(2,5-dimethoxy-3-nitrophenyl)-8-hydroxy-N,7,8,11-tetramethoxy-N,2,4,6,10-pentamethyl-4-undecenal
CAS No.:138694-27-6
Molecular Formula:C₃₂H₅₅NO₉Si
Molecular Weight:625.875
Hs Code.:

(2R,3R,4E,6S,7R,8S,10S,11R)-<(tert-Butyldimethylsilyl)oxy>-11-(2,5-dimethoxy-3-nitrophenyl)-8-hydroxy-N,7,8,11-tetramethoxy-N,2,4,6,10-pentamethyl-4-undecenal

Synonyms:(2R,3R,4E,6S,7R,8S,10S,11R)-<(tert-Butyldimethylsilyl)oxy>-11-(2,5-dimethoxy-3-nitrophenyl)-8-hydroxy-N,7,8,11-tetramethoxy-N,2,4,6,10-pentamethyl-4-undecenal

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Chemical Property of (2R,3R,4E,6S,7R,8S,10S,11R)-<(tert-Butyldimethylsilyl)oxy>-11-(2,5-dimethoxy-3-nitrophenyl)-8-hydroxy-N,7,8,11-tetramethoxy-N,2,4,6,10-pentamethyl-4-undecenal

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Technology Process of (2R,3R,4E,6S,7R,8S,10S,11R)-<(tert-Butyldimethylsilyl)oxy>-11-(2,5-dimethoxy-3-nitrophenyl)-8-hydroxy-N,7,8,11-tetramethoxy-N,2,4,6,10-pentamethyl-4-undecenal

There total 17 articles about (2R,3R,4E,6S,7R,8S,10S,11R)-<(tert-Butyldimethylsilyl)oxy>-11-(2,5-dimethoxy-3-nitrophenyl)-8-hydroxy-N,7,8,11-tetramethoxy-N,2,4,6,10-pentamethyl-4-undecenal 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: 95.0%

: 138721-96-7
(2R,3R,4E,6S,7R,8S,10S,11R)-3-(tert-Butyldimethylsilyloxy)-11-(2,5-dimethoxy-3-nitrophenyl)-N,7,8,11-tetramethoxy-N,2,4,6,10-pentamethyl-4-undecenamide

: 138694-27-6
(2R,3R,4E,6S,7R,8S,10S,11R)-<(tert-Butyldimethylsilyl)oxy>-11-(2,5-dimethoxy-3-nitrophenyl)-8-hydroxy-N,7,8,11-tetramethoxy-N,2,4,6,10-pentamethyl-4-undecenal

Guidance literature:: With diisobutylaluminium hydride;
DOI:10.1021/jo00030a006

Reference yield:

: 113453-29-5,138694-17-4
(2R,3R,4E)-3-Hydroxy-N-methoxy-N,2-dimethyl-5-phenyl-4-pentenamide

: 138694-27-6
(2R,3R,4E,6S,7R,8S,10S,11R)-<(tert-Butyldimethylsilyl)oxy>-11-(2,5-dimethoxy-3-nitrophenyl)-8-hydroxy-N,7,8,11-tetramethoxy-N,2,4,6,10-pentamethyl-4-undecenal

Guidance literature:: Multi-step reaction with 15 steps

1: 92 percent / NaH / tetrahydrofuran; dimethylformamide / 1 h / 0 °C

2: 85 percent / DIBAL-H / CH₂Cl₂; toluene / 1 h / -78 °C

3: 78 percent / toluene / 9 h / Heating

4: 90 percent / DIBAL-H / CH₂Cl₂; toluene / 1 h / -78 °C

5: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, 20 min, -60 deg C, 2) 2h 15 min, -60 deg C

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

8: 91 percent / imidazole / dimethylformamide / 18 h / Ambient temperature

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

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

11: 81 percent / Dess-Martin periodinane, pyridine / CH₂Cl₂ / 0.5 h / Ambient temperature

12: 70 percent / LiOH / tetrahydrofuran; H₂O / 1) 5 min, 0 deg C, 2) 3 h, r.t.

13: 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

14: 86 percent / Proton Sponge / CH₂Cl₂ / 3 h / Ambient temperature

15: 95 percent / DIBAL / tetrahydrofuran; toluene / 0.75 h / -78 °C

With pyridine; 1H-imidazole; lithium hydroxide; sodium periodate; osmium(VIII) oxide; zinc(II) tetrahydroborate; oxalyl dichloride; Proton Sponge; trimethylaluminum; titanium tetrachloride; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; cyclohexene; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00054a035

Reference yield:

: 138694-19-6
(2R,3R,4E)-3-Methoxy-2-methyl-5-phenyl-4-pentenal

: 138694-27-6
(2R,3R,4E,6S,7R,8S,10S,11R)-<(tert-Butyldimethylsilyl)oxy>-11-(2,5-dimethoxy-3-nitrophenyl)-8-hydroxy-N,7,8,11-tetramethoxy-N,2,4,6,10-pentamethyl-4-undecenal

Guidance literature:: Multi-step reaction with 13 steps

1: 78 percent / toluene / 9 h / Heating

2: 90 percent / DIBAL-H / CH₂Cl₂; toluene / 1 h / -78 °C

3: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, 20 min, -60 deg C, 2) 2h 15 min, -60 deg C

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

6: 91 percent / imidazole / dimethylformamide / 18 h / Ambient temperature

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

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

9: 81 percent / Dess-Martin periodinane, pyridine / CH₂Cl₂ / 0.5 h / Ambient temperature

10: 70 percent / LiOH / tetrahydrofuran; H₂O / 1) 5 min, 0 deg C, 2) 3 h, r.t.

11: 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

12: 86 percent / Proton Sponge / CH₂Cl₂ / 3 h / Ambient temperature

13: 95 percent / DIBAL / tetrahydrofuran; toluene / 0.75 h / -78 °C

With pyridine; 1H-imidazole; lithium hydroxide; sodium periodate; osmium(VIII) oxide; zinc(II) tetrahydroborate; oxalyl dichloride; Proton Sponge; trimethylaluminum; titanium tetrachloride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; cyclohexene; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00054a035