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. 2026 Aug 27;17:1901286. doi: 10.3389/fimmu.2026.1901286

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Copyright © 2026 Ma, Pequegnat, Hodgins, Sagermann, Ganeshapillai, Arar, Dawson, Frame, Wheadon, Chow, Arroyo and Monteiro.

This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.

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Reaction scheme depicting a multi-step synthetic pathway for carbohydrate derivatives, including molecular structures, stepwise reactions labeled a–l, chemical intermediates with substituents, and notations for reagents and protecting groups, used in complex oligosaccharide synthesis. — Reagent and conditions: (a) p-Anisaldehyde, NaOH (1 M), r.t.; (b) Ac₂O, pyridine, r.t.; (c) i. NH₃ in MeOH/toluene (1:3 v/v), r.t.; ii. Cl₃CCN, K₂CO₃, CH₂Cl_2, r.t., 62% starting from 1; (d) MeOH, 5% (v/v) AcCl, 0°C ~ r.t., 85%; (e) TrCl, pyridine, 55 °C, 78%; (f) AgOTf, MS, CH₂Cl₂, r.t., 67%; (g) Ac₂O, pyridine, r.t., 98%; (h) K₂CO₃, MeOH, r.t., 77%; (i) TrCl, pyridine, 55 °C, 65%; (j) 4, AgOTf, MS, CH₂Cl₂, r.t., 55%; (k) i. HOAc 80%, 80 °C, ii. NaOMe, MeOH, r.t., 60% in two steps; (l) i. HOAc 80%, 80 °C, ii. Ac₂O, pyridine, r.t., iii. NaOMe, MeOH, r.t., 57% in three steps.