337975-48-1

Upstream product

• 501-53-1 benzyl chloroformate 
• 1450984-45-8 (2R,3S)-2-((benzoxycarbonyl)amino)-1-[(tert-butyldimethylsilyl)oxy]hex-5-en-3-yl acetate 
• 656827-17-7 (2R,3S)-2-(benzyloxycarbonyl)amino-hex-5-ene-1,3-diol 
• 656827-16-6 (1S)-1-[(4R)-3-N-benzyloxycarbonyl-2,2-dimethyl-1,3-oxazolidin-4-yl]-but-3-en-1-ol 
• 656827-14-4 1-[(4R)-3-N-benzyloxycarbonyl-2,2-dimethyl-1,3-oxazolidin-4-yl]-but-3-en-1-one 
• 656827-13-3 (R)-benzyl-4-(methoxy(methyl)carbamoyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 1092473-80-7 (R)-benzyl 3-hydroxy-1-(methoxy(methyl)amino)-1-oxopropane-2-ylcarbamate 
• 6081-61-4 N-(benzyloxycarbonyl)-D-serine 
• 337975-51-6 Acetic acid (1S,2R)-2-(benzyl-benzyloxycarbonyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-1-oxiranylmethyl-propyl ester 

Downstream Products

• 1450984-46-9 C₂₆H₃₆N₂O₉Si 
• 95863-87-9 (2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)pyrrolidine-2-carboxylic acid 
• 95863-88-0 (2S,4S,5R)-4-Hydroxy-5-hydroxymethyl-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).