(S_S,2S)-(+)-N-[(tert-butyldimethylsilyl)oxy]-2-phenylacetylidene-p-toluenesulfinamide

Base Information

• Chemical Name: (S_S,2S)-(+)-N-[(tert-butyldimethylsilyl)oxy]-2-phenylacetylidene-p-toluenesulfinamide
• CAS No.: 310435-47-3
• Molecular Formula: C₂₁H₂₉NO₂SSi
• Molecular Weight: 387.618

Synonyms:(S_S,2S)-(+)-N-[(tert-butyldimethylsilyl)oxy]-2-phenylacetylidene-p-toluenesulfinamide

Chemical Property of (S_S,2S)-(+)-N-[(tert-butyldimethylsilyl)oxy]-2-phenylacetylidene-p-toluenesulfinamide

Chemical Property:

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Technology Process of (S_S,2S)-(+)-N-[(tert-butyldimethylsilyl)oxy]-2-phenylacetylidene-p-toluenesulfinamide

There total 1 articles about (S_S,2S)-(+)-N-[(tert-butyldimethylsilyl)oxy]-2-phenylacetylidene-p-toluenesulfinamide 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: 47.0%

(2S)-2-(tert-butyldimethylsilyloxy)-2-phenylacetaldehyde (133187-22-1) + (S)-p-toluenesulfinimide (188447-91-8) → (SS,2S)-(+)-N-[(tert-butyldimethylsilyl)oxy]-2-phenylacetylidene-p-toluenesulfinamide (310435-47-3)

Guidance literature:

With titanium(IV) tetraethanolate; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/jo000559h

Reference yield: 93.0%

diethylaluminium cyanide (5804-85-3) + (SS,2S)-(+)-N-[(tert-butyldimethylsilyl)oxy]-2-phenylacetylidene-p-toluenesulfinamide (310435-47-3) → (SS,2R,3S)-(+)-N-(p-toluenesulfinyl)-2-amino-[(tert-butyldimethylsilyl)oxy]-3-phenylpropionitrile (310435-58-6)

Guidance literature:

With isopropyl alcohol; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1021/jo000559h

Reference yield:

(SS,2S)-(+)-N-[(tert-butyldimethylsilyl)oxy]-2-phenylacetylidene-p-toluenesulfinamide (310435-47-3) → (2S,3S)-2-amino-3-hydroxy-3-phenylpropanoic acid (32946-42-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / i-PrOH / tetrahydrofuran / -78 - 20 °C

2: 52 percent / 3N HCl / 4 h / Heating

With hydrogenchloride; isopropyl alcohol; In tetrahydrofuran; 1: Addition / 2: Hydrolysis;

DOI:10.1021/jo000559h

upstream raw materials:

(2S)-2-(tert-butyldimethylsilyloxy)-2-phenylacetaldehyde

(S)-p-toluenesulfinimide

Downstream raw materials:

(S_S,2R,3S)-(+)-N-(p-toluenesulfinyl)-2-amino-[(tert-butyldimethylsilyl)oxy]-3-phenylpropionitrile

(2S,3S)-2-amino-3-hydroxy-3-phenylpropanoic acid

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