(S,E)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-5-iodo-N,2,4-trimethylpent-4-enamide

Base Information

Chemical Name:(S,E)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-5-iodo-N,2,4-trimethylpent-4-enamide
CAS No.:1132969-88-0
Molecular Formula:C₁₇H₂₄INO₂
Molecular Weight:401.288
Hs Code.:

Synonyms:(S,E)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-5-iodo-N,2,4-trimethylpent-4-enamide

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Chemical Property of (S,E)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-5-iodo-N,2,4-trimethylpent-4-enamide

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Technology Process of (S,E)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-5-iodo-N,2,4-trimethylpent-4-enamide

There total 1 articles about (S,E)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-5-iodo-N,2,4-trimethylpent-4-enamide 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: 88.0%

: 308088-80-4
(E)-3-bromo-1-iodo-2-methylprop-1-ene

: 192060-67-6
(1R,2R)-(-)-pseudoephedrinepropionamide

: 1132969-88-0
(S,E)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-5-iodo-N,2,4-trimethylpent-4-enamide

Guidance literature:: (1R,2R)-(-)-pseudoephedrinepropionamide; With n-butyllithium; diisopropylamine; lithium chloride; In tetrahydrofuran; hexane; at -78 - 20 ℃; Inert atmosphere;

(E)-3-bromo-1-iodo-2-methylprop-1-ene; In tetrahydrofuran; hexane; at 0 ℃; Inert atmosphere;
DOI:10.1002/chem.201102797

Reference yield:

: 1132969-88-0
(S,E)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-5-iodo-N,2,4-trimethylpent-4-enamide

: 1132970-13-8
(2Z,4E,6R,7S,8S,10E,12E,14S)-methyl 14-((4R,5S,6R)-6-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)-7-(formyloxy)-2,14-dimethoxy-4,6,8,10-tetramethyltetradeca-2,4,10,12-tetraenoate

Guidance literature:: Multi-step reaction with 16 steps

1.1: ammonia borane; n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / -78 - 20 °C / Inert atmosphere

2.1: pyridine; Dess-Martin periodane / methanol; dichloromethane / 2.75 h / 0 - 20 °C / Inert atmosphere

3.1: triethylamine / dichloromethane / 20 °C / Inert atmosphere

3.2: -78 °C / Inert atmosphere

4.1: 1H-imidazole; dmap / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

5.1: diisobutylaluminium hydride / hexane; dichloromethane / -78 - -40 °C / Inert atmosphere

6.1: NMO / dichloromethane / 0.5 h / 0 °C / Inert atmosphere; Molecular sieve

6.2: 0 - 20 °C / Inert atmosphere

7.1: toluene / 19 h / 65 °C / Inert atmosphere

8.1: diisobutylaluminium hydride / dichloromethane / -78 - -40 °C / Inert atmosphere

9.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / pyrrolidine / Inert atmosphere

9.2: 0 - 20 °C / Inert atmosphere

10.1: manganese(IV) oxide / dichloromethane / 8 h / 20 °C / Inert atmosphere

11.1: 18-crown-6 ether; potassium hexamethylsilazane / tetrahydrofuran / 0.08 h / 0 °C / Inert atmosphere

11.2: 2.5 h / 0 °C / Inert atmosphere

12.1: (-)-N-methylephedrine; zinc trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / toluene / 35 h / 20 °C / Inert atmosphere

12.2: 17 h / 20 °C / Inert atmosphere

13.1: tris(acetonitrile)pentamethylcyclopentadienyl-ruthenium(I) hexafluorophosphate; Triethoxysilane / dichloromethane / 0 - 20 °C / Inert atmosphere

13.2: 0 - 20 °C / Inert atmosphere

14.1: tetrahydrofuran; N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

15.1: pyridine hydrogenfluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

16.1: dmap / dichloromethane / 20 °C / Inert atmosphere

16.2: 0.25 h / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; dmap; manganese(IV) oxide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; ammonia borane; 18-crown-6 ether; Triethoxysilane; NMO; tris(acetonitrile)pentamethylcyclopentadienyl-ruthenium(I) hexafluorophosphate; (-)-N-methylephedrine; potassium hexamethylsilazane; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; diisopropylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyrrolidine; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 3.1: Masamune anti-aldol reaction / 11.1: Horner-Wadsworth-Emmons olefination / 11.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1002/chem.201102797

Reference yield:

: 1132969-88-0
(S,E)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-5-iodo-N,2,4-trimethylpent-4-enamide

: 1132969-98-2
methyl (2Z,4E,6R,7S,8S,10E,12E,14S,15R,16S,17R,18S,19S)-19-(tert-butyldiphenylsilyloxy)-7,15,17-trihydroxy-2,14-dimethoxy-4,6,8,10,16,18-hexamethylicosa-2,4,10,12-tetraenoate

Guidance literature:: Multi-step reaction with 17 steps

1.1: ammonia borane; n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / -78 - 20 °C / Inert atmosphere

2.1: pyridine; Dess-Martin periodane / methanol; dichloromethane / 2.75 h / 0 - 20 °C / Inert atmosphere

3.1: triethylamine / dichloromethane / 20 °C / Inert atmosphere

3.2: -78 °C / Inert atmosphere

4.1: 1H-imidazole; dmap / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

5.1: diisobutylaluminium hydride / hexane; dichloromethane / -78 - -40 °C / Inert atmosphere

6.1: NMO / dichloromethane / 0.5 h / 0 °C / Inert atmosphere; Molecular sieve

6.2: 0 - 20 °C / Inert atmosphere

7.1: toluene / 19 h / 65 °C / Inert atmosphere

8.1: diisobutylaluminium hydride / dichloromethane / -78 - -40 °C / Inert atmosphere

9.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / pyrrolidine / Inert atmosphere

9.2: 0 - 20 °C / Inert atmosphere

10.1: manganese(IV) oxide / dichloromethane / 8 h / 20 °C / Inert atmosphere

11.1: 18-crown-6 ether; potassium hexamethylsilazane / tetrahydrofuran / 0.08 h / 0 °C / Inert atmosphere

11.2: 2.5 h / 0 °C / Inert atmosphere

12.1: (-)-N-methylephedrine; zinc trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / toluene / 35 h / 20 °C / Inert atmosphere

12.2: 17 h / 20 °C / Inert atmosphere

13.1: tris(acetonitrile)pentamethylcyclopentadienyl-ruthenium(I) hexafluorophosphate; Triethoxysilane / dichloromethane / 0 - 20 °C / Inert atmosphere

13.2: 0 - 20 °C / Inert atmosphere

14.1: tetrahydrofuran; N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

15.1: pyridine hydrogenfluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

16.1: dmap / dichloromethane / 20 °C / Inert atmosphere

16.2: 0.25 h / 20 °C / Inert atmosphere

17.1: CSA / methanol / 20 °C / Inert atmosphere

17.2: Inert atmosphere

With pyridine; 1H-imidazole; dmap; manganese(IV) oxide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; ammonia borane; 18-crown-6 ether; Triethoxysilane; NMO; tris(acetonitrile)pentamethylcyclopentadienyl-ruthenium(I) hexafluorophosphate; (-)-N-methylephedrine; potassium hexamethylsilazane; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; diisopropylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyrrolidine; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 3.1: Masamune anti-aldol reaction / 11.1: Horner-Wadsworth-Emmons olefination / 11.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1002/chem.201102797