Full Stereocontrol in α-Glycosidation of 3-Deoxy-d-manno-2-octulosonic Acid (Kdo) Using Macrobicyclic Glycosyl Donors,Organic Letters

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Full Stereocontrol in α-Glycosidation of 3-Deoxy-d-manno-2-octulosonic Acid (Kdo) Using Macrobicyclic Glycosyl Donors
Organic Letters ( IF 4.9 ) Pub Date : 2022-11-18 , DOI: 10.1021/acs.orglett.2c03542
Shogo Hamajima ₁ , Naoko Komura _{1,

2} , Hide-Nori Tanaka _{1,

2} , Akihiro Imamura _{1,

2,

3} , Hideharu Ishida _{1,

2,

3} , Haruka Noguchi ₄ , Tsuyoshi Ichiyanagi ₄ , Hiromune Ando _{1,

2}

Affiliation

We describe a method for the α-selective glycosidation of 3-deoxy-d-manno-2-octulosonic acid (Kdo) using a macrobicyclic Kdo donor as the precursor of a bridgehead oxocarbenium ion, whose stereoselectivity is not affected by the substrate structure and reaction conditions. Strapping Kdo via tethering in the α-configuration at the C1 and C5 positions completely blocked nucleophilic attack to the β-face of the anomeric center by sterically hindering the bicyclic system, realizing full α-selectivity during glycosidation.

中文翻译：

使用大双环糖基供体对 3-脱氧-d-甘露-2-辛糖酸 (Kdo) 的 α-糖苷化进行完全立体控制

我们描述了一种使用大双环 Kdo 供体作为桥头氧碳鎓离子前体的 3-脱氧-d-甘露糖 -2-octulosonic 酸 (Kdo) 的 α-选择性糖苷化方法，其立体选择性不受底物结构的影响，并且反应条件。通过束缚在 C1 和 C5 位置的 α-构型中束缚 Kdo，通过空间位阻双环系统完全阻断了对异头中心 β-面的亲核攻击，在糖苷化过程中实现了完全的 α-选择性。

更新日期：2022-11-18

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