Publication Type
Peer Reviewed Journal
Mandatory Citation Fields
Gemma, Emiliano,Lahmann, Martina,Oscarson, Stefan;
2005
Synthesis of the tetrasaccharide a-D-Glcp-(1->3)-a-D-Manp-(1->2)-a-D-Manp-(1->2)-a-D-Manp recognized by Calreticulin/Calnexin
Published
Optional Fields
Please enter separate search keywords on separate lines
340
16
2558
2562
The title compd. as its Me glycoside was efficiently synthesized using a block synthesis approach. Halide-assisted glycosylation between 6-O-acetyl-2,3,4-tri-O-benzyl-a-D-glucopyranosyl iodide and Et 2-O-acetyl-4,6-di-O-benzyl-1-thio-a-D-mannopyranoside using triphenylphosphine oxide as promoter yielded, with complete a-selectivity, a disaccharide building block in high yield. The per-benzylated deriv. of this proved to be an excellent donor affording 88% of the protected target tetrasaccharide in an NIS/AgOTf-promoted coupling to a known Me dimannoside acceptor. Deprotection through catalytic hydrogenolysis then gave the target compd. in 47% overall yield. [on SciFinder (R)]
Grant Details
  • © University College Dublin 2010
  • Privacy
  • Policy
  • Freedom of Information