Efficient Synthesis of -D-Mannosides and 详细信息    查看全文

• 作者：Hai Dong ; Zhichao Pei ; Marcus Angelin ; Styrbj&ouml ; rn Bystr&ouml ; m ; Olof Ramstr&ouml ; m
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：May 11, 2007
• 年：2007
• 卷：72
• 期：10
• 页码：3694 - 3701
• 全文大小：188K
• 年卷期：v.72,no.10(May 11, 2007)
• ISSN：1520-6904

文摘

A neighboring equatorial ester group plays a highly important role in the Lattrell-Dax (nitrite-mediated)carbohydrate epimerization reaction, inducing the formation of inversion compounds in good yields. Onthe basis of this effect, efficient synthetic routes to -D-mannosides and -D-talosides, from thecorresponding -D-galactosides and -D-glucosides, have been designed. The present routes are basedon multiple regioselective acylation via the respective stannylene intermediates, followed by inversionsto the corresponding manno- and talopyranoside structures by nitrite or acetate substitution. It was foundthat the ester group was able to induce the inversion of its two neighboring groups in high yields followingeither a double parallel or a double serial inversion process. By combination of direct inversion, andneighboring- as well as remote-group participation, several -D-mannoside and -D-taloside derivativeswere very conveniently obtained in good yields.