title: Synthesis of a versatile building block for the preparation of 6-N-derivatized α-galactosyl ceramides: rapid access to biologically active glycolipids.
abstract: A concise route to the 6-azido-6-deoxy-α-galactosyl-phytosphingosine derivative 9 is reported. Orthogonal protection of the two amino groups allows elaboration of 9 into a range of 6-N-derivatized α-galactosyl ceramides by late-stage introduction of the acyl chain of the ceramide and the 6-N-group in the sugar headgroup. Biologically active glycolipids 6 and 8 have been synthesized to illustrate the applicability of the approach.
authors.affiliation: School of Biosciences, University of Birmingham, Edgbaston, Birmingham B15 2TT, United Kingdom.
authors.forename: Peter J
authors.initials: PJ
authors.lastname: Jervis
authors.forename: Liam R
authors.initials: LR
authors.lastname: Cox
authors.forename: Gurdyal S
authors.initials: GS
authors.lastname: Besra
mesh_terms: D002241:Carbohydrates / Q000737:chemistry*; D005699:Galactosylceramides / Q000138:chemical synthesis* / Q000737:chemistry*; D006017:Glycolipids / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D002241:Carbohydrates; D005699:Galactosylceramides; D006017:Glycolipids; C493154:alpha-galactosylceramide; C103873:KRN 7000