Sanki Aditya K, Suresh Cheravakkattu G, Falgune Usha D, Pathak Tanmaya
Organic Chemistry Division (Synthesis), National Chemical Laboratory, Pune 411 008, India.
Org Lett. 2003 Apr 17;5(8):1285-8. doi: 10.1021/ol0342047.
[structure: see text] This is the first report on the diastereoselective addition of carbon nucleophiles to vinyl sulfone-modified hex-2-enopyranosides and pent-2-enofuranosides. Nucleophiles add to the C-2 position from a direction opposite to that of the disposition of the anomeric methoxy group. This novel concept of anomeric configuration-directed stereocontrolled carbon-carbon bond formation in vinyl sulfone-modified carbohydrates is general in nature and has been implemented in the synthesis of new hexopyranosyl and pentofuranosyl branched-chain sugars and densely functionalized carbohydrates.
[结构：见正文] 这是关于碳亲核试剂向乙烯基砜修饰的己-2-烯吡喃糖苷和戊-2-烯呋喃糖苷进行非对映选择性加成的首次报道。亲核试剂从与异头甲氧基排列方向相反的方向加成到C-2位。乙烯基砜修饰的碳水化合物中这种由异头构型导向的立体控制碳-碳键形成的新概念本质上具有普遍性，并已应用于新的己吡喃糖基和戊呋喃糖基支链糖以及高度官能化碳水化合物的合成中。
