title: The Crotylation Way to Glycosphingolipids: Synthesis of Analogues of KRN7000.
abstract: A synthesis of glycosphingolipids that centers on the reaction of O- and C-glycosyl crotylstannanes and relatively simple lipid aldehydes is described. The modularity of this strategy and versatility of the crotylation products make this an attractive approach to diverse, highly substituted libraries. The methodology is applied to analogues of the potent imunostimulatory glycolipid KRN7000, including O-, methylene-, and fluoromethine-linked isosteres with diastereomeric ceramide segments and 2-amido substitutes.
authors: Hunter College, The City University of New York (CUNY) , 695 Park Avenue, New York, New York 10021, United States.|The Graduate Center, CUNY , 365 Fifth Avenue, New York, New York 10016, United States.
authors: Ahmad S
authors: AS
authors: Altiti
authors: Hunter College, The City University of New York (CUNY) , 695 Park Avenue, New York, New York 10021, United States.|The Graduate Center, CUNY , 365 Fifth Avenue, New York, New York 10016, United States.
authors: Stewart
authors: S
authors: Bachan
authors: Hunter College, The City University of New York (CUNY) , 695 Park Avenue, New York, New York 10021, United States.|The Graduate Center, CUNY , 365 Fifth Avenue, New York, New York 10016, United States.
authors: David R
authors: DR
authors: Mootoo
mesh_terms: D005699:Galactosylceramides / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation
chemical_list: D005699:Galactosylceramides; C103873:KRN 7000