The Synthesis of (2S,3R)-2-Hydroxymethylpiperidin-3-ol, a Fragment of the Alkaloid Swainsonine
- 1 January 1990
- journal article
- research article
- Published by CSIRO Publishing in Australian Journal of Chemistry
- Vol. 43 (7) , 1183-1193
- https://doi.org/10.1071/ch9901183
Abstract
Methyl α- and β-D-galactopyranoside have been converted into methyl 4,6-di-O-benzyl-2,3-dideoxy-α- and -β-D-threo-hexoside , and subsequent treatment with ethanedithiol gives the same alcohol. Tosylation and azide displacement gives, after hydrolysis, an azido aldehyde which is transformed under reducing conditions into the title piperidine . The synthetic piperidine is an ineffective inhibitor of α-D- mannosidase.Keywords
This publication has 6 references indexed in Scilit:
- Studies related to the use of fused bipyranoses for synthesis of polypropionate arraysCarbohydrate Research, 1988
- Synthesis of the α-Mannosidase inhibitors swainsonine [(1S, 2R, 8R, 8aR)-1,2,8-trihydroxyoctahydroindolizine] and 1,4-dideoxy-1,4-imino-d-mannitol from mannoseTetrahedron, 1987
- Synthesis of Tetrasaccharides Related to the O-Specific Determinants of Salmonella Serogroups A, B and D1.Acta Chemica Scandinavica, 1984
- Inhibition of lysosomal α-mannosidase by swainsonine, an indolizidine alkaloid isolated from Swainsona canescensBiochemical Journal, 1980
- Reactions of relevance to the chemistry of aminoglycoside antibiotics. Part 11. Preparation of olefins from vicinal diolsJournal of the Chemical Society, Perkin Transactions 1, 1979
- Action of zinc dust and sodium iodide in N,N-dimethylformamide on contiguous, secondary sulfonyloxy groups: a simple method for introducing nonterminal unsaturationCarbohydrate Research, 1965