Direct β-Mannosylation of Primary Alcohol Acceptors: Trisaccharide Iteration Assembly of β-1,6-Oligomannosides Corresponding to Kakelokelose.
Direct β-Mannosylation of Primary Alcohol Acceptors: Trisaccharide Iteration Assembly of β-1,6-Oligomannosides Corresponding to Kakelokelose.
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DOI：
10.1021/acs.orglett.1c04363
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发表时间：
2022-01
期刊：
影响因子：
5.2
通讯作者：
Peng Wang;Junlin Wang;W. Yin;Xianyang Wang;Ni Song;S. Ren;Ming Li
中科院分区：
文献类型：
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作者：
Peng Wang;Junlin Wang;W. Yin;Xianyang Wang;Ni Song;S. Ren;Ming Li
使用正交保护的甘露糖基α-邻己炔基苯甲酸酯（OABz）供体实现伯醇的金（I）催化的立体选择性β-糖基化，所述OABz供体不含用于常规构建β-甘露糖苷键的4，6-O-束缚基团。这种方法的潜力通过通过收敛策略首次组装β-1，6-三/六-/九甘露糖苷和相关硫酸化同系物来展示。该合成的特点是α-三甘露糖基OABz供体的立体控制的β-糖基化和后期磺化。本工作有望加快β-1，6-甘露聚糖及其功能化衍生物的制备。
Gold(I)-catalyzed stereoselective β-glycosylation of primary alcohols is achieved using the orthogonally protected mannosyl α-ortho-hexynylbenzoate (OABz) donors devoid of 4,6-O-tethering groups used in conventionally constructing β-mannosidic bonds. The potential of this methodology is showcased by the first assembly of β-1,6-tri/hexa-/nonamannosides and related sulfated congeners through a convergent strategy. The synthesis features the stereocontrolled β-glycosylation of α-trimannosyl OABz donors and the late-stage sulfonation. This work is expected to expedite the preparation of β-1,6-mannans and functionalized derivatives.