156365-93-4

Basic information

• Product Name: (2S,4S,5R)-2-(1S)-(1-hydroxy-1-phenyl)ethyl-4-methyl-5-phenyl-3-tert-butoxycarbonyloxazolidine
• CAS NO: 156365-93-4
• Molecular Weight: 383.488
• Mol File: 156365-93-4.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (2S,4S,5R)-2-(1S)-(1-hydroxy-1-phenyl)ethyl-4-methyl-5-phenyl-3-tert-butoxycarbonyloxazolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,4S,5R)-2-(1S)-(1-hydroxy-1-phenyl)ethyl-4-methyl-5-phenyl-3-tert-butoxycarbonyloxazolidine(156365-93-4)
• EPA Substance Registry System: (2S,4S,5R)-2-(1S)-(1-hydroxy-1-phenyl)ethyl-4-methyl-5-phenyl-3-tert-butoxycarbonyloxazolidine(156365-93-4)

Safety Data

• Hazardous Substances Data: 156365-93-4(Hazardous Substances Data)

Upstream product

• 156365-95-6 (2S,4S,5R)-4-methyl-2-(1-oxo)ethyl-5-phenyl-3-tert-butoxycarbonyloxazolidine 
• 156365-82-1 (2S,4S,5R)-2-ethoxycarbonyl-4-methyl-5-phenyl-3-tert-butoxycarbonyloxazolidine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 100-58-3 phenylmagnesium bromide 
• 156365-84-3 (2S,4S,5R)-2-(N-methoxy-N-methyl)-carbamoyl-4-methyl-5-phenyl-3-tert-butoxycarbonyloxazolidine 
• 156365-83-2 (2S,4S,5R)-2-carboxy-4-methyl-5-phenyl-3-tert-butoxycarbonyloxazolidine 
• 492-41-1 (1R,2S)-norephedrine 

Downstream Products

• 2406-22-6 (2S)-2-phenylpropane-1,2-diol 
• 69489-14-1 (S)-(+)-2-hydroxy-2-phenylpropanal 

Relevant articles and documents

N-Boc 2-acyloxazolidines: Useful precursors to enantiopure 1,2-diols via highly diastereoselective nucleophilic additions

N-Boc 2-Acyloxazolidines were synthesized from norephedrine and phenylglycinol. This preparation involves: (i) a transformation or the above β-amino alcohols into N-Boc 2-ethoxycarbonyloxazolidines, (ii) the formation of the corresponding Weinreb amides and, (iii) a reaction between these amides and organometallic reagents. Such diastereomerically pure heterocycles react cleanly with various nucleophilic reagents (Grignard reagents, sodium borohydride and allylsilane) to afford the corresponding alcohols. Treatment of these hydroxyoxazolidines with trifluoro acetic acid, followed by hydrolysis and reduction of the intermediate α-hydroxy aldehydes afforded 1,2-diols. The overall transformation exhibited in most cases a complete diastereoselectivity which can be explained by a chelated model for the nucleophilic addition.