Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 22, Pages 10600-10616Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b02106
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Funding
- JSPS KAKENHI in Middle Molecular Strategy [15H05836]
- JSPS KAKENHI [16H01885, 16H05924]
- Grants-in-Aid for Scientific Research [16H05924, 15H05836, 16H01885] Funding Source: KAKEN
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A chemical synthesis of a core fucose containing N-glycan was achieved. Asparagine was introduced at an early stage of the synthesis, and the sugar chain was convergently elongated. As for the fragment synthesis, we reinvestigated alpha-sialylation, beta-mannosylation, and N-glycosylation to reveal that precise temperature control was essential for these glycosylations. Intermolecular hydrogen bonds involving acetamide groups were found to reduce the reactivity in glycosylations: the protection of NHAc as NAc2 dramatically improved the reactivity. The dodecasaccharide-asparagine framework was constructed via the (4 + 4) glycosylation and the (4 + 8) glycosylation using the tetrasaccharide donor and the tetrasaccharide-asparagine acceptor. An ether-type solvent enhanced the yields of these key glycosylations between large substrates. After the whole deprotection of the dodecasaccharide, the target N-glycan was obtained.
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