853014-83-2Relevant academic research and scientific papers
Glucosamine derived DISAL donors for stereoselective glycosylations under neutral conditions
Grathe, Susanne,Thygesen, Mikkel B.,Larsen, Kim,Petersen, Lars,Jensen, Knud J.
, p. 1439 - 1448 (2007/10/03)
DISAL (methyl 3,5-dinitrosalicylate) D-glucosyl, D-galactosyl, D-mannosyl, and L-quinovosyl donors have previously provided the efficient glycosylation of a range of substrates under either strictly neutral, mildly basic, or very mildly Lewis acidic (LiClO4) conditions. Herein we report the synthesis of new glucosamine DISAL donors, carrying N-TCP, -Troc, or -TFAc protecting groups, and their use in β-(1,2-trans) selective glycosylations, primarily in NMP in the absence of any added Lewis acids, or in CH 3NO2 with LiClO4. Finally, precise microwave heating proved effective in promoting the difficult glycosylation of the 3-OH of a glucosamine derivative.
