Chong Pek Y, Roush William R
Department of Chemistry, University of Michigan, Ann Arbor 48109, USA.
Org Lett. 2002 Dec 12;4(25):4523-6. doi: 10.1021/ol027066e.
[structure: see text] Studies on the glycosidation reactions of conformationally constrained glycosyl imidates 8a and 8b were performed to evaluate the possible involvement of "conformationally inverted" oxonium ion intermediates in glycosidation reactions with 2-deoxy-2-iodo-glucopyranosyl donors. The mechanistic implications of this study are discussed, and intermediates 23 and 24 are invoked to rationalize the observed beta-selectivities.
[结构：见正文] 对构象受限的糖基亚氨酸酯8a和8b的糖苷化反应进行了研究，以评估“构象反转”的氧鎓离子中间体在与2-脱氧-2-碘吡喃葡萄糖基供体的糖苷化反应中可能的参与情况。讨论了该研究的机理意义，并引入中间体23和24来解释观察到的β选择性。
