Journal
CARBOHYDRATE RESEARCH
Volume 338, Issue 23, Pages 2557-2569Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2003.06.002
Keywords
phosphatidylinositol; phosphatidylinositol mannoside; synthesis; glycosidation; structural assignment
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Two strategies towards the synthesis of phosphatidylinositol mannosides (PIMs) were elaborated which permit selective access to the O-l-, O-2-, and the O-6 position of the myo-inositol residue. Starting materials are 1,2:5,6- and 1,2:4,5-di-O-cyclohexylidene-DL-myo-inositol, respectively. In the latter case, the required assignment to the D- or L-series is based on the transformation of one enantiomer into known ( -)-liriodentritol. The efficiency and potential versatility of the two approaches is exemplified in the synthesis Of PIMS (D)-1a and its pseudoenantiomer (L)-1b, both having myristoyl residues as part of the phosphatidyl moiety. (C) 2003 Elsevier Ltd. All rights reserved.
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