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

Base Information

• Chemical Name: (R_S,2S,3R)-(-)-N-(p-toluenesulfinyl)-2-amino-[(tert-butyldimethylsilyl)oxy]-3-phenylpropionitrile
• CAS No.: 310435-60-0
• Molecular Formula: C₂₂H₃₀N₂O₂SSi
• Molecular Weight: 414.644

Synonyms:(R_S,2S,3R)-(-)-N-(p-toluenesulfinyl)-2-amino-[(tert-butyldimethylsilyl)oxy]-3-phenylpropionitrile

Chemical Property of (R_S,2S,3R)-(-)-N-(p-toluenesulfinyl)-2-amino-[(tert-butyldimethylsilyl)oxy]-3-phenylpropionitrile

Chemical Property:

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Technology Process of (R_S,2S,3R)-(-)-N-(p-toluenesulfinyl)-2-amino-[(tert-butyldimethylsilyl)oxy]-3-phenylpropionitrile

There total 3 articles about (R_S,2S,3R)-(-)-N-(p-toluenesulfinyl)-2-amino-[(tert-butyldimethylsilyl)oxy]-3-phenylpropionitrile 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: 100.0%

diethylaluminium cyanide (5804-85-3) + (RS,2R)-(-)-N-[(tert-butyldimethylsilyl)oxy]-2-phenylacetylidene-p-toluenesulfinamide (310435-48-4) → (RS,2S,3R)-(-)-N-(p-toluenesulfinyl)-2-amino-[(tert-butyldimethylsilyl)oxy]-3-phenylpropionitrile (310435-60-0)

Guidance literature:

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

DOI:10.1021/jo000559h

Reference yield:

(R)-2-(t-butyldimethylsilyloxy)-2-phenylacetaldehyde (130115-07-0) → (RS,2S,3R)-(-)-N-(p-toluenesulfinyl)-2-amino-[(tert-butyldimethylsilyl)oxy]-3-phenylpropionitrile (310435-60-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 47 percent / Ti(OEt)4 / CH₂Cl₂ / 2 h / 20 °C

2: 100 percent / i-PrOH / tetrahydrofuran / -78 - 20 °C

With titanium(IV) tetraethanolate; isopropyl alcohol; In tetrahydrofuran; dichloromethane; 1: Condensation / 2: Addition;

DOI:10.1021/jo000559h

Reference yield:

(R)-p-toluenesulfinamide (247089-85-6) → (RS,2S,3R)-(-)-N-(p-toluenesulfinyl)-2-amino-[(tert-butyldimethylsilyl)oxy]-3-phenylpropionitrile (310435-60-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 47 percent / Ti(OEt)4 / CH₂Cl₂ / 2 h / 20 °C

2: 100 percent / i-PrOH / tetrahydrofuran / -78 - 20 °C

With titanium(IV) tetraethanolate; isopropyl alcohol; In tetrahydrofuran; dichloromethane; 1: Condensation / 2: Addition;

DOI:10.1021/jo000559h

upstream raw materials:

diethylaluminium cyanide

(R_S,2R)-(-)-N-[(tert-butyldimethylsilyl)oxy]-2-phenylacetylidene-p-toluenesulfinamide

(R)-2-(t-butyldimethylsilyloxy)-2-phenylacetaldehyde

(R)-p-toluenesulfinamide

Downstream raw materials:

(2R;3R)-2-amino-3-hydroxy-3-phenylpropionic acid

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