91229-96-8

Upstream product

• 45214-91-3 N^α-(tert-butyloxycarbonyl)-γ-methyl L-glutamic acid 
• 30924-93-7 α-benzyl N^α-(tert-butyloxycarbonyl)-L-glutamate 
• 1499-55-4 glutamic acid γ-methyl ester 
• 91230-01-2 O^α-benzyl N^α-(tert-butyloxycarbonyl)-γ-<2-(trimethylsilyl)ethyl>-L-glutamic acid α-hydroxamate 
• 91229-92-4 α-benzyl N^α-(tert-butyloxycarbonyl)-γ-<2-(trimethylsilyl)ethyl>-L-glutamate 
• 91229-99-1 O^α-benzyl N^α-(tert-butyloxycarbonyl)-γ-methyl-L-glutamic acid α-hydroxamate 
• 91229-93-5 O^α-benzyl N^α-(tert-butyloxycarbonyl)-L-glutamic acid α-hydroxamate 
• 91230-00-1 N^α-(tert-butyloxycarbonyl)-γ-<2-(trimethylsilyl)ethyl>-L-glutamic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 622-33-3 N-benzyloxyamine 
• 251987-04-9 (5S)-1-tert-butoxycarbonyl-5-(1-ethoxy)ethoxymethyl pyrrolidin-2-one 
• 251987-13-0 (4S)-N-benzyloxy-4-(N-tert-butoxycarbonyl)amino-5-[(1-ethoxy)ethoxy]pentanamide 
• 91229-95-7 O^α-benzyl N^α-(tert-butyloxycarbonyl)-γ-(2-thioxo-1,3-thiazolidin-3-yl)-L-glutamic acid α-hydroxamate 

Downstream Products

• 172913-96-1 (5S)-5-[(tert-butoxycarbonyl)amino]piperidin-2-one 
• 154148-70-6 (S)-5-aminopiperidin-2-one 
• 91229-98-0 1-(benzyloxy)-5-<(tert-butyloxycarbonyl)amino>-piperidone 

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.

Enantioselective Synthesis of (S)-5-Aminopiperidin-2-one from (S)-Pyroglutaminol

(5S)-5-aminopiperidin-2-one and several derivatives were synthesized from (S)-pyroglutaminol through ring opening and Mitsunobu reaction as the key steps.