751456-32-3

Upstream product

• 251987-28-7 methyl (2R,3R,4R)-4-(N-tert-butoxycarbonyl)amino-2,3-epoxy-5-[(1-ethoxy)ethoxy]pentanoate 
• 251986-99-9 (3R,4R,5R)-1-tert-butoxycarbonyl-3,4-epoxy-5-[(1-ethoxy)ethoxymethyl]pyrrolidin-2-one 
• 251987-41-4 (R)-[(4R,5S)-4-(1-Ethoxy-ethoxymethyl)-2-oxo-oxazolidin-5-yl]-hydroxy-acetic acid methyl ester 
• 251986-95-5 (3R,4R,5R)-3,4-epoxy-5-[(1-ethoxy)ethoxymethyl]pyrrolidin-2-one 
• 154631-82-0 (2R,5R,6R,7R)-6,7-epoxy-2-phenyl-3-oxa-1-aza-bicyclo<3.3.0>octane-8-one 
• 154495-23-5 (1R,4R,5R)-4-Hydroxymethyl-6-oxa-3-aza-bicyclo[3.1.0]hexan-2-one 

Relevant academic research and scientific papers

Regio- and stereoselective opening of oxiranes through neighbouring group participation: Stereocontrolled synthesis of enantiopure hydroxylated oxazolidin-2-ones

The regio- and stereo-selective ring opening of (S)-pyroglutaminol derived epoxides provides an effective route to protected syn,syn-aminodiol units. The procedure involves the chemoselective aminolysis or alcoholysis of (3R,4R,5R)-N-(tert-butoxycarbonyl)-3,4-epoxy-5-[(1- ethoxy)ethoxymethyl]pyrrolidin-2-one (10), followed by the formation in quantitative yield of oxazolidinone intermediates, through the mediation of neighbouring N-Boc groups. The practical synthetic interest of this route is illustrated by the example of (3R,4S,5R)-3,4-diacetoxy-5- (acetoxymethyl)pyrrolidin-2-one which should serve as useful building block in further syntheses.