251987-24-3

Basic information

• Product Name: (2R,3R,4R)-N-benzyloxy-4-(N-tert-butoxycarbonyl)amino-2,3-epoxy-5-[(1-ethoxy)ethoxy]pentanamide
• Synonyms: (2R,3R,4R)-N-benzyloxy-4-(N-tert-butoxycarbonyl)amino-2,3-epoxy-5-[(1-ethoxy)ethoxy]pentanamide
• CAS NO: 251987-24-3
• Molecular Weight: 424.494
• Mol File: 251987-24-3.mol

Chemical Properties

• CAS DataBase Reference: (2R,3R,4R)-N-benzyloxy-4-(N-tert-butoxycarbonyl)amino-2,3-epoxy-5-[(1-ethoxy)ethoxy]pentanamide(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4R)-N-benzyloxy-4-(N-tert-butoxycarbonyl)amino-2,3-epoxy-5-[(1-ethoxy)ethoxy]pentanamide(251987-24-3)
• EPA Substance Registry System: (2R,3R,4R)-N-benzyloxy-4-(N-tert-butoxycarbonyl)amino-2,3-epoxy-5-[(1-ethoxy)ethoxy]pentanamide(251987-24-3)

Safety Data

• Hazardous Substances Data: 251987-24-3(Hazardous Substances Data)

Upstream product

• 622-33-3 N-benzyloxyamine 
• 251986-99-9 (3R,4R,5R)-1-tert-butoxycarbonyl-3,4-epoxy-5-[(1-ethoxy)ethoxymethyl]pyrrolidin-2-one 
• 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 articles and documents

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.