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Synthesis of the tetrasaccharide α-D-Glcp-(1→3)-α-D-Manp-(1→2)-α-D-Manp-(1→2)-α-D-Manp recognised by Calreticulin/Calnexin
2005 (English)In: Carbohydrate Research, Vol. 340, no 16, p. 2558-2562Article in journal (Refereed) Published
Abstract [en]

The title compound as its methyl glycoside was efficiently synthesized using a block synthesis approach. Halide-assisted glycosidations between 6-O-acetyl-2,3,4-tri-O-benzyl-α-d-glucopyranosyl iodide and ethyl 2-O-acetyl-4,6-di-O-benzyl-1-thio-α-d-mannopyranoside using triphenylphosphine oxide as promoter yielded, with complete α-selectivity, a disaccharide building block in high yield. The perbenzylated derivative of this proved to be an excellent donor affording 88% of the protected target tetrasaccharide in an NIS/AgOTf-promoted coupling to a known methyl dimannoside acceptor. Deprotection through catalytic hydrogenolysis then gave the target compound in 47% overall yield.

Place, publisher, year, edition, pages
Elsevier BV , 2005. Vol. 340, no 16, p. 2558-2562
Keywords [en]
Calreticulin substrates; Iodide glycosyl donors; Triphenylphosphine oxide promotion; Thioglycoside block donor
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-305736DOI: 10.1016/j.carres.2005.09.001ISI: 000233150000012PubMedID: 16169533Scopus ID: 2-s2.0-26844484751OAI: oai:DiVA.org:kth-305736DiVA, id: diva2:1617289
Note

QC 20211206

Available from: 2021-12-06 Created: 2021-12-06 Last updated: 2022-06-25Bibliographically approved

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Lahmann, Martina

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