150779-99-0

Upstream product

• 58479-61-1 tert-butylchlorodiphenylsilane 
• 220223-44-9 4-(tert-Butoxycarbonyl-methoxycarbonylmethyl-amino)-butyric acid methyl ester 
• 220223-47-2 (2S,3S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(imidazole-1-carbothioyloxy)-piperidine-1-carboxylic acid tert-butyl ester 
• 150779-88-7 (2S,3S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester 
• 150779-90-1 tert-butyl (R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)piperidine-1-carboxylate 
• 122019-53-8 3-oxo-1,2-piperidinedicarboxylic acid 1-(1,1-dimethylethyl) 2-methyl ester 
• 152230-79-0 (2R,3S)-1-tert-butyloxycarbonyl-2-methoxycarbonyl-3-hydroxy-piperidine 
• 150779-89-8 (2S,3S)-tert-butyl 3-hydroxy-2-(hydroxymethyl)piperidine-1-carboxylate 
• 98-59-9 p-toluenesulfonyl chloride 
• 856015-17-3 (R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-piperidine 

Downstream Products

• 60343-64-8 (R)-(1-tosylpiperidin-2-yl)methanol 

Relevant academic research and scientific papers

β-Hydroxypiperidinecarboxylates: Additions to the chiral pool from bakers' yeast reductions of β-ketopiperidinecarboxylates

Reduction of the piperidine keto esters 16-19 using fermenting bakers' yeast provides high yields of the corresponding hydroxy esters 20, 26, 32 and 37 respectively, exclusively as the cis-diastereoisomers and with good levels (≥80%) of enantiomeric enrichment. The relative stereochemistries of the products were deduced from NMR data while the absolute configurations were determined by degradation to known piperidinemethanol derivatives or, in the case of hydroxy ester 37, by homologation to (R)-3-quinuclidinol 41b.

New Members of the Chiral Pool: β-Hydroxypiperidine Carboxylates from Baker's Yeast Reduction of the Corresponding Keto-esters

Baker's yeast reductions of the keto-piperidinecarboxylates 2 and 6 leads to the corresponding hydroxy-esters 3 and 7a in good chemical yields and with >99percent d.e. and >93percent e.e. in both cases.