ChemInform Abstract: Stereoselective Synthesis of L‐Deoxyaltronojirimycin (VII) from L‐Serine

Abstract

Carbohydrates U 0500 Stereoselective Synthesis of L-Deoxyaltronojirimycin (VII) from L-Serine -[involving ring-closing metathesis and stereoselective epoxidation as key steps]. -(RENGASAMY, R.; CURTIS-LONG, M. J.; RYU, H. W.; OH, K. Y.; PARK*, K. H.; Bull. Korean Chem.

Piperidine azasugars displaying competitive α-rhamnosidase inhibition and their kinetic mechanism

“…Based upon our previous studies, which readily produced 5 stereodefined azasugars, the C4 stereocenter was confirmed to be S for good inhibition [Rengasamy et al, 2009]. Most importantly, compound 1 was shown to be a The hydrolytic activity of α-rhamnosidase as a function of compound 1 concentration (0, ù; 3.1 μM, ø; 6.2 μM, Ă; 12.5 μM, ÿ, respectively).…”

“…The starting compound 6, (3R,4S)-3-Hydroxy-4-N-allyl-NBoc-amino-1-pentene, has been achieved as a single diastereomer without racemization via vinyl Grignard addition to N-Boc-N-allyl aminoaldehyde from enantio pure L-alanine [Rengasamy et al, 2008]. The other starting compound 9 was started from L-serine and proceeded via a highly stereoselective neucleophilic addition to an aminoaldehyde equivalent and ring closing metathesis using Grubbs II catalyst [Rengasamy et al, 2009]. The preparation of tetrahydropyridene 7 was achieved in 78% yield via ring closing metathesis using Grubbs II catalyst (Scheme 1).…”