Abstract

The synthesis of gram quantities of the TF antigen (β-ᴅ-Gal-(1→3)-α-ᴅ-GalNAc) and its 3’-sulfated analogue with a TEG-N₃ spacer attached is described. The synthesis of the TF antigen comprises seven steps, from a known N-Troc-protected galactosamine donor, with an overall yield of 31%. Both the spacer (85%) and the galactose moiety (79%) were introduced using thioglycoside donors in NIS/AgOTf-promoted glycosylation reactions. The 3’-sulfate was finally introduced through tin activation in benzene/DMF followed by treatment with a sulfur trioxide–trimethylamine complex in a 66% yield.

Beilstein J. Org. Chem. 2024, 20, 173–180. doi:10.3762/bjoc.20.17

摘要

描述了克量的 TF 抗原 (β-ᴅ-Gal-(1→3)-α-ᴅ-GalNAc) 及其带有 TEG-N _{3间隔基的 3'-硫酸化类似物的合成。}TF抗原的合成包括七个步骤，来自已知的N -Troc保护的半乳糖胺供体，总产率为31%。在 NIS/AgOTf 促进的糖基化反应中，使用硫代糖苷供体引入间隔基 (85%) 和半乳糖部分 (79%)。最终通过苯/DMF 中的锡活化引入 3'-硫酸盐，然后用三氧化硫-三甲胺络合物处理，产率 66%。

贝尔斯坦 J. 组织。化学。 2024, 20, 173–180。doi:10.3762/bjoc.20.17