(S)-N-[(2E,4E,8E,10E,14E)-(1R,6S,12S,17S)-6,12-Bis-(tert-butyl-dimethyl-silanyloxy)-3,9,15,17-tetramethyl-16-oxo-cycloheptadeca-2,4,8,10,14-pentaenyl]-2-(tert-butyl-diphenyl-silanyloxy)-propionamide

Base Information

• Chemical Name: (S)-N-[(2E,4E,8E,10E,14E)-(1R,6S,12S,17S)-6,12-Bis-(tert-butyl-dimethyl-silanyloxy)-3,9,15,17-tetramethyl-16-oxo-cycloheptadeca-2,4,8,10,14-pentaenyl]-2-(tert-butyl-diphenyl-silanyloxy)-propionamide
• CAS No.: 328381-96-0
• Molecular Formula: C₅₂H₈₁NO₅Si₃
• Molecular Weight: 884.475

Synonyms:(S)-N-[(2E,4E,8E,10E,14E)-(1R,6S,12S,17S)-6,12-Bis-(tert-butyl-dimethyl-silanyloxy)-3,9,15,17-tetramethyl-16-oxo-cycloheptadeca-2,4,8,10,14-pentaenyl]-2-(tert-butyl-diphenyl-silanyloxy)-propionamide

Chemical Property of (S)-N-[(2E,4E,8E,10E,14E)-(1R,6S,12S,17S)-6,12-Bis-(tert-butyl-dimethyl-silanyloxy)-3,9,15,17-tetramethyl-16-oxo-cycloheptadeca-2,4,8,10,14-pentaenyl]-2-(tert-butyl-diphenyl-silanyloxy)-propionamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of (S)-N-[(2E,4E,8E,10E,14E)-(1R,6S,12S,17S)-6,12-Bis-(tert-butyl-dimethyl-silanyloxy)-3,9,15,17-tetramethyl-16-oxo-cycloheptadeca-2,4,8,10,14-pentaenyl]-2-(tert-butyl-diphenyl-silanyloxy)-propionamide

There total 30 articles about (S)-N-[(2E,4E,8E,10E,14E)-(1R,6S,12S,17S)-6,12-Bis-(tert-butyl-dimethyl-silanyloxy)-3,9,15,17-tetramethyl-16-oxo-cycloheptadeca-2,4,8,10,14-pentaenyl]-2-(tert-butyl-diphenyl-silanyloxy)-propionamide 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: 59.0%

{(5E,7E,11E,13E)-(3S,4R,9S,15S)-9,15-Bis-(tert-butyl-dimethyl-silanyloxy)-4-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-propionylamino]-1,3,6,12-tetramethyl-2,17-dioxo-heptadeca-5,7,11,13-tetraenyl}-phosphonic acid diethyl ester (328381-95-9) → (S)-N-[(2E,4E,8E,10E,14E)-(1R,6S,12S,17S)-6,12-Bis-(tert-butyl-dimethyl-silanyloxy)-3,9,15,17-tetramethyl-16-oxo-cycloheptadeca-2,4,8,10,14-pentaenyl]-2-(tert-butyl-diphenyl-silanyloxy)-propionamide (328381-96-0)

Guidance literature:

With barium dihydroxide; In tetrahydrofuran;

DOI:10.1002/1521-3773(20001215)39:24<4612::AID-ANIE4612>3.0.CO;2-C

Reference yield:

(4S,5R)-5-(tert-butyldiphenylsilyloxymethyl)-4-methyl-4,5-dihydrofuran (221007-97-2) → (S)-N-[(2E,4E,8E,10E,14E)-(1R,6S,12S,17S)-6,12-Bis-(tert-butyl-dimethyl-silanyloxy)-3,9,15,17-tetramethyl-16-oxo-cycloheptadeca-2,4,8,10,14-pentaenyl]-2-(tert-butyl-diphenyl-silanyloxy)-propionamide (328381-96-0)

Guidance literature:

Multi-step reaction with 20 steps

1.1: 87 percent / H₂O / CH₂Cl₂ / 20 °C / Irradiation

2.1: 77 percent / toluene / Heating

3.1: 98 percent / TBAF / tetrahydrofuran

4.1: aq. NaIO₄ / tetrahydrofuran

5.1: NaBH₄ / CH₂Cl₂; methanol

6.1: imidazole / toluene

7.1: LiHMDS / tetrahydrofuran / -78 °C

7.2: 92 percent / tetrahydrofuran

8.1: 80 percent / H₂ / Pd/BaSO₄ / ethyl acetate / 4137.18 Torr

9.1: 88 percent / L-selectride / tetrahydrofuran / -78 - 20 °C

10.1: 2,6-lutidine / CH₂Cl₂

11.1: LiBr / tetrahydrofuran / 20 °C

12.1: nBuLi / tetrahydrofuran / -78 °C

12.2: 97 percent / tetrahydrofuran / -78 - 20 °C

13.1: 85 percent / PPTS; H₂O / methanol

14.1: 89 percent / aq. H₂O₂; (NH₄)6Mo₇O₂₄*4H₂O / ethanol / 0 - 20 °C

15.1: LDA / tetrahydrofuran / 0.08 h / -78 °C

15.2: 72 percent / tetrahydrofuran / -78 - 20 °C

16.1: 98 percent / Dess-Martin periodinane; MaHCO₃ / CH₂Cl₂ / 20 °C

17.1: LDA / tetrahydrofuran / 1 h / -78 °C

17.2: CeCl₃ / tetrahydrofuran / 1 h / -78 °C

17.3: 61 percent / tetrahydrofuran / -78 - 20 °C

18.1: 77 percent / MeLi / diethyl ether / -10 - 20 °C

19.1: 74 percent / Dess-Martin periodinane; MaHCO₃ / CH₂Cl₂

20.1: 59 percent / aq. Ba(OH)2 / tetrahydrofuran

With 1H-imidazole; 2,6-dimethylpyridine; ammonium heptamolybdate; barium dihydroxide; sodium tetrahydroborate; sodium periodate; n-butyllithium; tetrabutyl ammonium fluoride; water; methyllithium; hydrogen; dihydrogen peroxide; pyridinium p-toluenesulfonate; L-Selectride; Dess-Martin periodane; lithium bromide; lithium hexamethyldisilazane; lithium diisopropyl amide; Pd-BaSO₄; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; ethyl acetate; toluene; 16.1: Dess-Martin oxidation / 19.1: Dess-Martin oxidation;

DOI:10.1002/1521-3773(20001215)39:24<4612::AID-ANIE4612>3.0.CO;2-C

Reference yield:

(3S,4S,5R)-<5-(tert-butyldiphenylsilyloxymethyl)-2-hydroxy-4-methyltetrahydrofuran-3-yl>carbamic acid benzyl ester (221007-99-4) → (S)-N-[(2E,4E,8E,10E,14E)-(1R,6S,12S,17S)-6,12-Bis-(tert-butyl-dimethyl-silanyloxy)-3,9,15,17-tetramethyl-16-oxo-cycloheptadeca-2,4,8,10,14-pentaenyl]-2-(tert-butyl-diphenyl-silanyloxy)-propionamide (328381-96-0)

Guidance literature:

Multi-step reaction with 19 steps

1.1: 77 percent / toluene / Heating

2.1: 98 percent / TBAF / tetrahydrofuran

3.1: aq. NaIO₄ / tetrahydrofuran

4.1: NaBH₄ / CH₂Cl₂; methanol

5.1: imidazole / toluene

6.1: LiHMDS / tetrahydrofuran / -78 °C

6.2: 92 percent / tetrahydrofuran

7.1: 80 percent / H₂ / Pd/BaSO₄ / ethyl acetate / 4137.18 Torr

8.1: 88 percent / L-selectride / tetrahydrofuran / -78 - 20 °C

9.1: 2,6-lutidine / CH₂Cl₂

10.1: LiBr / tetrahydrofuran / 20 °C

11.1: nBuLi / tetrahydrofuran / -78 °C

11.2: 97 percent / tetrahydrofuran / -78 - 20 °C

12.1: 85 percent / PPTS; H₂O / methanol

13.1: 89 percent / aq. H₂O₂; (NH₄)6Mo₇O₂₄*4H₂O / ethanol / 0 - 20 °C

14.1: LDA / tetrahydrofuran / 0.08 h / -78 °C

14.2: 72 percent / tetrahydrofuran / -78 - 20 °C

15.1: 98 percent / Dess-Martin periodinane; MaHCO₃ / CH₂Cl₂ / 20 °C

16.1: LDA / tetrahydrofuran / 1 h / -78 °C

16.2: CeCl₃ / tetrahydrofuran / 1 h / -78 °C

16.3: 61 percent / tetrahydrofuran / -78 - 20 °C

17.1: 77 percent / MeLi / diethyl ether / -10 - 20 °C

18.1: 74 percent / Dess-Martin periodinane; MaHCO₃ / CH₂Cl₂

19.1: 59 percent / aq. Ba(OH)2 / tetrahydrofuran

With 1H-imidazole; 2,6-dimethylpyridine; ammonium heptamolybdate; barium dihydroxide; sodium tetrahydroborate; sodium periodate; n-butyllithium; tetrabutyl ammonium fluoride; water; methyllithium; hydrogen; dihydrogen peroxide; pyridinium p-toluenesulfonate; L-Selectride; Dess-Martin periodane; lithium bromide; lithium hexamethyldisilazane; lithium diisopropyl amide; Pd-BaSO₄; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; ethyl acetate; toluene; 15.1: Dess-Martin oxidation / 18.1: Dess-Martin oxidation;

DOI:10.1002/1521-3773(20001215)39:24<4612::AID-ANIE4612>3.0.CO;2-C

upstream raw materials:

{(5E,7E,11E,13E)-(3S,4R,9S,15S)-9,15-Bis-(tert-butyl-dimethyl-silanyloxy)-4-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-propionylamino]-1,3,6,12-tetramethyl-2,17-dioxo-heptadeca-5,7,11,13-tetraenyl}-phosphonic acid diethyl ester

(4S,5R)-5-(tert-butyldiphenylsilyloxymethyl)-4-methyl-4,5-dihydrofuran

(3S,4S,5R)-<5-(tert-butyldiphenylsilyloxymethyl)-2-hydroxy-4-methyltetrahydrofuran-3-yl>carbamic acid benzyl ester

benzoic acid 3-(tert-butyl-dimethyl-silanyloxy)-4-oxo-butyl ester

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