Genomics Research Center, Academia Sinica, Taipei 115, Taiwan.
Org Biomol Chem. 2011 Oct 26;9(22):7655-8. doi: 10.1039/c1ob06056b. Epub 2011 Sep 16.
Specific deuterated reference compounds were prepared to probe the stereoselectivity of the reductive ring opening of carbohydrate-based benzylidene-type acetals. AlD(3) revealed a retentive stereoselectivity probably through the rare S(N)i (internal nucleophilic substitution) mechanism. An S(N)1-like mechanism occurs in the acid-promoted regioselective BD(3)·THF- or Et(3)SiD-reductive ring opening.
特定氘代参考化合物被制备来探测基于碳水化合物的苄叉型缩醛的还原开环的立体选择性。AlD(3) 表现出保留的立体选择性，可能是通过罕见的 S(N)i（内部亲核取代）机制。在酸促进的区域选择性 BD(3)·THF-或 Et(3)SiD-还原开环中，发生 S(N)1 样机制。
