Glycosyl Sulfonates Beyond Triflates
Glycosyl Sulfonates Beyond Triflates
复制标题
三氟甲磺酸盐以外的糖基磺酸盐
DOI：
10.1002/tcr.202100141
复制
发表时间：
2021
期刊：
影响因子：
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通讯作者：
Bennett, Clay S.
中科院分区：
文献类型：
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作者：
Bennett, Clay S.
虽然糖基三氟甲磺酸酯在许多化学糖基化反应中经常被用作中间体，但其他糖基磺酸酯的化学性质仍然相对未被研究。考虑到磺酸酯的反应性可以跨越几个数量级，这代表了立体选择性糖基化反应开发的未开发资源。这个个人账户描述了我们的实验室努力利用这种反应性来开发β特异性糖基化反应。最初的研究导致了2-脱氧糖甲苯磺酸酯作为β-糖苷合成的高选择性供体的开发，该方法已被我们小组和其他人用于构建脱氧糖寡糖和天然产物，并取得了巨大成功。随后的研究表明，将磺酸盐的反应性与糖供体的反应性“匹配”，导致与一系列底物的高度选择性的SN 2-糖基化。
While glycosyl triflates are frequently invoked as intermediates in many chemical glycosylation reactions, the chemistry of other glycosyl sulfonates remains comparatively underexplored. Given the reactivity of sulfonates can span several orders of magnitude, this represents an untapped resource for the development of stereoselective glycosylation reactions. This personal account describes our laboratories efforts to take advantage of this reactivity to develop β‐specific glycosylation reactions. Initial investigations led to the development of 2‐deoxy‐sugar tosylates as highly selective donors for β‐glycoside synthesis, an approach which has been used to great success by our group and others for the construction of deoxy‐sugar oligosaccharides and natural products. Subsequent studies demonstrate that “matching” the reactivity of the sulfonate to that of the sugar donor leads to highly selective SN2‐glycosylations with a range of substrates.