95863-88-0

Upstream product

• 95863-87-9 (2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)pyrrolidine-2-carboxylic acid 
• 501-53-1 benzyl chloroformate 
• 337975-48-1 benzyl (2S,4S,5R)-4-acetoxy-2-carboxy-5-[(tert-butyldimethylsilyloxy)methyl]pyrrolidine-1-carboxylate 
• 337975-50-5 benzyl (2R,3S,5S)-3-acetoxy-2-((tert-butyldimethylsilyloxy)methyl)-5-(hydroxymethyl)pyrrolidine-1-carboxylate 
• 337975-51-6 Acetic acid (1S,2R)-2-(benzyl-benzyloxycarbonyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-1-oxiranylmethyl-propyl ester 
• 6081-61-4 N-(benzyloxycarbonyl)-D-serine 
• 1092473-80-7 (R)-benzyl 3-hydroxy-1-(methoxy(methyl)amino)-1-oxopropane-2-ylcarbamate 
• 656827-13-3 (R)-benzyl-4-(methoxy(methyl)carbamoyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 656827-14-4 1-[(4R)-3-N-benzyloxycarbonyl-2,2-dimethyl-1,3-oxazolidin-4-yl]-but-3-en-1-one 
• 656827-16-6 (1S)-1-[(4R)-3-N-benzyloxycarbonyl-2,2-dimethyl-1,3-oxazolidin-4-yl]-but-3-en-1-ol 
• 656827-17-7 (2R,3S)-2-(benzyloxycarbonyl)amino-hex-5-ene-1,3-diol 
• 1450984-45-8 (2R,3S)-2-((benzoxycarbonyl)amino)-1-[(tert-butyldimethylsilyl)oxy]hex-5-en-3-yl acetate 
• 1053286-13-7 (2R,4S,5R)-5-Formyl-4-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 
• 145473-26-3 methyl N-(carbobenzyloxy)-4-hydroxy-5-(1',2',3',4'-tetrahydroxybutyl)prolinate 

Downstream Products

• 95863-93-7 (2S,4S,5R)-4-Hydroxy-5-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester; compound with dicyclohexyl-amine 
• 95863-87-9 (2R,4S,5S)-4-Hydroxy-5-hydroxymethyl-pyrrolidine-2-carboxylic acid 
• 110658-38-3 (2S,4S,5S)-4-Hydroxy-5-hydroxymethyl-pyrrolidine-2-carboxylic acid 
• 95863-94-8 (2S,4S,5R)-4-Acetoxy-5-acetoxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester; compound with dicyclohexyl-amine 
• 95863-90-4 (1S,4S,6R)-6-Hydroxymethyl-3-oxo-2-oxa-5-aza-bicyclo[2.2.1]heptane-5-carboxylic acid benzyl ester 
• 95863-87-9 (2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)pyrrolidine-2-carboxylic acid 
• 95863-95-9 (2S,4S,5R)-4-Hydroxy-5-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-(3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl) ester 
• 95863-89-1 (2S,4S,5R)-4-Acetoxy-5-acetoxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 

Relevant academic research and scientific papers

Polyhydroxylated pyrrolidine and 2-oxapyrrolizidine as glycosidase inhibitors

Using D-serine as a chiral precursor, a polyhydroxylated pyrrolidine (1), its derivatives bearing carboxylate, phosphate and phosphonate groups (2-4) and an oxapyrrolizidine (5) were synthesized. The pyrrolidine ring was formed by intramolecular amino-mercuration. The bicyclic scaffold of oxapyrrolizidine was further constructed by an intramolecular attack of the carbamate group on the iodomethyl group. Compounds 1 and 5 were found to inhibit β-glucosidase and α-galactosidase, respectively, in a competitive manner, whereas compounds 2, 3 and 4 did not produce significant inhibition against glycosidases. The Royal Society of Chemistry 2013.

An efficient stereoselective synthesis of (2S,4S,5R)-(-)-bulgecinine

N-Benzyl-N-carbobenzyloxy-O-tert-butyldimethylsilyl-d-serinal (6) was reacted under Barbier conditions with allyl bromide affording diastereoselectively (82:18) the anti-adduct 5, which was subsequently transformed into (2S,4S,5R)-(-)-bulgecinine (1).

STRUCTURES OF BULGECINS, BACTERIAL METABOLITES WITH BULGE-INDUCING ACTIVITY

The structure of bulgecin A, a bacterial metabolite with bulge-inducing activity, was determined chemically and spectrometrically to be 4-O-(2'-acetyamino-2'-deoxy-4'-O-hydroxysulfonyl-β-D-glucopyranosyl)-(2S,4S,5R)-4-hydroxy-5-hydroxymethylprolyltaurine