Publication Type
Publication Type
Peer Reviewed Journal
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Authors
Gemma, Emiliano,Lahmann, Martina,Oscarson, Stefan;
Year
2005
Month
Journal
Title
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
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Published
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Volume
340
Issue
16
Start Page
2558
End Page
2562
Abstract
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)]
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