| Title | Synthesis and kinetic analysis of the N-acetylhexosaminidase inhibitor XylNAc-isofagomine |
| Publication Type | Journal Article |
| Year of Publication | 2005 |
| Authors | Knapp, S, Yang, CH, Pabbaraja, S, Rempel, B, Reid, S, Withers, SG |
| Journal | JOURNAL OF ORGANIC CHEMISTRY |
| Volume | 70 |
| Pagination | 7715-7720 |
| Date Published | SEP 16 |
| ISSN | 0022-3263 |
| Abstract | An efficient 10-step preparation from 4-methoxypyridine of (2R,3R,4R)-2-acetamido-3,4-dihydroxypiperidine ({''}XyINAe-isofagomine{''}) 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. |
| DOI | 10.1021/jo051117e |
