(4S,5S)-2-Methyl-4-(trisisopropylsilyloxymethyl)-5-phenyl-4,5-dihydro-1,3-oxazole

Base Information

• Chemical Name: (4S,5S)-2-Methyl-4-(trisisopropylsilyloxymethyl)-5-phenyl-4,5-dihydro-1,3-oxazole
• CAS No.: 175477-34-6
• Molecular Formula: C₂₀H₃₃NO₂Si
• Molecular Weight: 347.573

Synonyms:(4S,5S)-2-Methyl-4-(trisisopropylsilyloxymethyl)-5-phenyl-4,5-dihydro-1,3-oxazole

Chemical Property of (4S,5S)-2-Methyl-4-(trisisopropylsilyloxymethyl)-5-phenyl-4,5-dihydro-1,3-oxazole

Chemical Property:

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Technology Process of (4S,5S)-2-Methyl-4-(trisisopropylsilyloxymethyl)-5-phenyl-4,5-dihydro-1,3-oxazole

There total 2 articles about (4S,5S)-2-Methyl-4-(trisisopropylsilyloxymethyl)-5-phenyl-4,5-dihydro-1,3-oxazole 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: 93.0%

(4S,5S)-4-Hydroxymethyl-2-methyl-5-phenyl-4,5-dihydro-1,3-oxazole (53732-41-5) + triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → (4S,5S)-2-Methyl-4-(trisisopropylsilyloxymethyl)-5-phenyl-4,5-dihydro-1,3-oxazole (175477-34-6)

Guidance literature:

With triethylamine; In dichloromethane; Ambient temperature; 1.) 5 min, 2.) 15 min;

DOI:10.1039/p19960000333

Reference yield:

(1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1) → (4S,5S)-2-Methyl-4-(trisisopropylsilyloxymethyl)-5-phenyl-4,5-dihydro-1,3-oxazole (175477-34-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / CH₂Cl₂ / 16 h / Ambient temperature

2: 93 percent / Et₃N / CH₂Cl₂ / Ambient temperature; 1.) 5 min, 2.) 15 min

With triethylamine; In dichloromethane;

DOI:10.1039/p19960000333

Reference yield: 64.0%

(-)-menthyl p-toluenesulfinate (1517-82-4) + (4S,5S)-2-Methyl-4-(trisisopropylsilyloxymethyl)-5-phenyl-4,5-dihydro-1,3-oxazole (175477-34-6) → (4S,5S)-5-Phenyl-2-((R)-toluene-4-sulfinylmethyl)-4-triisopropylsilanyloxymethyl-4,5-dihydro-oxazole (175671-58-6)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; 1.) -78 deg C, 1 h, 2.) -78 deg C, 2 h;

DOI:10.1039/p19960000333

upstream raw materials:

(4S,5S)-4-Hydroxymethyl-2-methyl-5-phenyl-4,5-dihydro-1,3-oxazole

triisopropylsilyl trifluoromethanesulfonate

(1S,2S)-2-amino-1-phenyl-1,3-diol

Downstream raw materials:

(4S,5S)-5-Phenyl-2-((S)-toluene-4-sulfinylmethyl)-4-triisopropylsilanyloxymethyl-4,5-dihydro-oxazole

(4S,5S)-5-Phenyl-2-((R)-toluene-4-sulfinylmethyl)-4-triisopropylsilanyloxymethyl-4,5-dihydro-oxazole

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