145100-52-3

Upstream product

• 27248-04-0 4-((trimethylsilyl)oxy)pyridine 
• 121675-89-6 (2S)-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-2-n-propyl-5,6-didehydro-piperidin-4-one 
• 213197-97-8 1,4-dihydro-1-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-pyridin-4(1H)-one 
• 501-53-1 benzyl chloroformate 
• 767321-57-3 (2S)-2,6-dipropyl-1-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)piperidin-4-one 

Downstream Products

• 146254-02-6 (2S,6R)-4-Chloro-5-formyl-2,6-dipropyl-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester 
• 145100-57-8 (2S,6R)-2,6-Dipropyl-4-trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester 

Relevant academic research and scientific papers

Stereoselective synthesis of enantiomerically pure piperidine derivatives by N-galactosylation of pyridones

Stereoselective desymmetrization of 4-pyridone has been achieved through selective N-galactosylation, activation of the N-(galactosyl)pyridone by O-silylation and immediate addition of Grignard compounds. Chiral piperidine derivatives, e.g. (S)-(+)-coniine and (5S,9S)-(+)-indolozidine 167B, were synthesised in enantiomerically pure form using these highly regio- and stereoselective reactions. After N-galactosylation of 2-pyridone and O-silylation of the N-galactosyl-2-pyridone, addition of a Grignard compound proceeded with high 1,4-regioselectivity and complete diastereoselectivity, to furnish 4-substituted 5,6-dehydro-2-piperidones. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.