(2S,4R)-5-((tert-butyldimethylsilyl)oxy)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N,2,4-trimethylpentanamide

Base Information

• Chemical Name: (2S,4R)-5-((tert-butyldimethylsilyl)oxy)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N,2,4-trimethylpentanamide
• CAS No.: 1352995-01-7
• Molecular Formula: C₂₃H₄₁NO₃Si
• Molecular Weight: 407.669

Synonyms:(2S,4R)-5-((tert-butyldimethylsilyl)oxy)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N,2,4-trimethylpentanamide

Chemical Property of (2S,4R)-5-((tert-butyldimethylsilyl)oxy)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N,2,4-trimethylpentanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R)-5-((tert-butyldimethylsilyl)oxy)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N,2,4-trimethylpentanamide

There total 1 articles about (2S,4R)-5-((tert-butyldimethylsilyl)oxy)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N,2,4-trimethylpentanamide 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%

(2S)-(+)-(tert-butyl-dimethyl)-(3-iodo-2-methyl-propoxy)-silane (168335-78-2) + (1R,2R)-(-)-pseudoephedrinepropionamide (192060-67-6) → (2S,4R)-5-((tert-butyldimethylsilyl)oxy)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N,2,4-trimethylpentanamide (1352995-01-7)

Guidance literature:

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

(2S)-(+)-(tert-butyl-dimethyl)-(3-iodo-2-methyl-propoxy)-silane; In tetrahydrofuran; at 0 ℃; Inert atmosphere;

DOI:10.3762/bjoc.7.161

Reference yield:

(2S,4R)-5-((tert-butyldimethylsilyl)oxy)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N,2,4-trimethylpentanamide (1352995-01-7) → (3Z,5S,6S,7R,9E,11R,13S,14R,15S,16Z)-14-((tert-butyldimethylsilyl)oxy)-17-iodo-6-((4-methoxybenzyl)oxy)-5,7,11,13,15-pentamethylheptadeca-3,9,16-trien-8-one (1352995-23-3)

Guidance literature:

Multi-step reaction with 10 steps

1.1: borane-ammonia complex; n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 0 - 20 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

3.1: diethylzinc; palladium diacetate; triphenylphosphine / tetrahydrofuran; hexane / -78 - -20 °C / Inert atmosphere

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere

5.1: 2,6-dimethylpyridine / dichloromethane / -78 - 20 °C / Inert atmosphere

6.1: tert.-butyl lithium / tetrahydrofuran; pentane / -78 °C / Inert atmosphere

6.2: -78 - 20 °C / Inert atmosphere

7.1: 2-nitrobenzenesulfonyl hydrazide; triethylamine / tetrahydrofuran; isopropyl alcohol / 16 h / 20 °C / Inert atmosphere

8.1: pyridine hydrofluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

9.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere

10.1: barium(II) hydroxide / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

10.2: Inert atmosphere

With 2,6-dimethylpyridine; n-butyllithium; borane-ammonia complex; oxalyl dichloride; pyridine hydrofluoride; 2-nitrobenzenesulfonyl hydrazide; tetrabutyl ammonium fluoride; tert.-butyl lithium; diethylzinc; palladium diacetate; sodium hydrogencarbonate; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; diisopropylamine; triphenylphosphine; barium(II) hydroxide; In tetrahydrofuran; hexane; dichloromethane; isopropyl alcohol; pentane; 2.1: Swern oxidation / 2.2: Swern oxidation / 3.1: Marshall alkylation / 10.1: Horner-Wadsworth-Emmons olefination / 10.2: Horner-Wadsworth-Emmons olefination;

DOI:10.3762/bjoc.7.161

Reference yield:

(2S,4R)-5-((tert-butyldimethylsilyl)oxy)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N,2,4-trimethylpentanamide (1352995-01-7) → (3Z,5S,6S,7R,11S,13S,14R,15S,16Z)-14-((tert-butyldimethylsilyl)oxy)-17-iodo-6-((4-methoxybenzyl)oxy)-5,7,11,13,15-pentamethylheptadeca-3,16-dien-8-one (1352995-25-5)

Guidance literature:

Multi-step reaction with 11 steps

1.1: borane-ammonia complex; n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 0 - 20 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

3.1: diethylzinc; palladium diacetate; triphenylphosphine / tetrahydrofuran; hexane / -78 - -20 °C / Inert atmosphere

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere

5.1: 2,6-dimethylpyridine / dichloromethane / -78 - 20 °C / Inert atmosphere

6.1: tert.-butyl lithium / tetrahydrofuran; pentane / -78 °C / Inert atmosphere

6.2: -78 - 20 °C / Inert atmosphere

7.1: 2-nitrobenzenesulfonyl hydrazide; triethylamine / tetrahydrofuran; isopropyl alcohol / 16 h / 20 °C / Inert atmosphere

8.1: pyridine hydrofluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

9.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere

10.1: barium(II) hydroxide / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

10.2: Inert atmosphere

11.1: Stryker's reagent / toluene / 0 - 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; n-butyllithium; borane-ammonia complex; oxalyl dichloride; pyridine hydrofluoride; 2-nitrobenzenesulfonyl hydrazide; tetrabutyl ammonium fluoride; tert.-butyl lithium; diethylzinc; palladium diacetate; sodium hydrogencarbonate; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; diisopropylamine; triphenylphosphine; barium(II) hydroxide; In tetrahydrofuran; hexane; dichloromethane; isopropyl alcohol; toluene; pentane; 2.1: Swern oxidation / 2.2: Swern oxidation / 3.1: Marshall alkylation / 10.1: Horner-Wadsworth-Emmons olefination / 10.2: Horner-Wadsworth-Emmons olefination;

DOI:10.3762/bjoc.7.161

upstream raw materials:

(2S)-(+)-(tert-butyl-dimethyl)-(3-iodo-2-methyl-propoxy)-silane

(1R,2R)-(-)-pseudoephedrinepropionamide

Downstream raw materials:

(3Z,5S,6S,7R,9E,11R,13S,14R,15S,16Z)-14-((tert-butyldimethylsilyl)oxy)-17-iodo-6-((4-methoxybenzyl)oxy)-5,7,11,13,15-pentamethylheptadeca-3,9,16-trien-8-one

(3Z,5S,6S,7R,11S,13S,14R,15S,16Z)-14-((tert-butyldimethylsilyl)oxy)-17-iodo-6-((4-methoxybenzyl)oxy)-5,7,11,13,15-pentamethylheptadeca-3,16-dien-8-one

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