@article { ISI:000231859000034, title = {Synthesis and kinetic analysis of the N-acetylhexosaminidase inhibitor XylNAc-isofagomine}, journal = {JOURNAL OF ORGANIC CHEMISTRY}, volume = {70}, number = {19}, year = {2005}, month = {SEP 16}, pages = {7715-7720}, abstract = {An efficient 10-step preparation from 4-methoxypyridine of (2R,3R,4R)-2-acetamido-3,4-dihydroxypiperidine ({{\textquoteright}{\textquoteright}}XyINAe-isofagomine{{\textquoteright}{\textquoteright}}) in optically active form is described. Key steps include an enantioselective reduction with catecholborane/(S)-2-methyl-CBS-oxazaborolidine, and a stereo-selective pseudo-glycosylation of lithium azide by a cyclic sulfite ester. The title compound showed a K-i = 21 mu M when evaluated against the N-acetyl-beta-hexosaminidase from Streptomyces plicatus.}, issn = {0022-3263}, doi = {10.1021/jo051117e}, author = {Knapp, S and Yang, CH and Pabbaraja, S and Rempel, B and Reid, S and Withers, SG} }