The iodocyclization of homoallylic trichloroacetimidates derived from α-C-allyl galactoside were investigated. In line with the stereochemical trend observed for less substituted non-glycosylated frameworks, E and Z substrates delivered stereoselectively the 1,3-anti and 1,3-syn amino alcohol motifs, respectively. These products are advanced precursors to C-glycosides of the potent immunostimulatory glycolipid KRN7000.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5240635 | PMC |
| http://dx.doi.org/10.1016/j.carres.2015.02.005 | DOI Listing |
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C-glycosphingolipid precursors via iodocyclization of homoallyic trichloroacetimidates.
Carbohydr Res
April 2015
Department of Chemistry, Hunter College, 695 Park Avenue, New York, NY 10065, USA; The Graduate Center, CUNY, 365 5th Avenue, New York, NY 10016, USA. Electronic address:
The iodocyclization of homoallylic trichloroacetimidates derived from α-C-allyl galactoside were investigated. In line with the stereochemical trend observed for less substituted non-glycosylated frameworks, E and Z substrates delivered stereoselectively the 1,3-anti and 1,3-syn amino alcohol motifs, respectively. These products are advanced precursors to C-glycosides of the potent immunostimulatory glycolipid KRN7000.
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