A convenient synthesis of pseudoglycosides via a Ferrier-type rearrangement using metal-free H₃PO₄ catalyst

详细信息    查看全文

• 作者：Bala Kishan Gorityala ; Shuting Cai ; Rujee Lorpitthaya ; Jimei Ma ; Kalyan Kumar Pasunooti ; Xue-Wei Liu
• 刊名：Tetrahedron Letters
• 出版年：2009
• 出版时间：11 February 2009
• 年：2009
• 卷：50
• 期：6
• 页码：676-679
• 全文大小：172 K

文摘

A mild and efficient synthesis of pseudoglycals has been developed using a metal-free catalytic system. Phosphoric acid proved to be an excellent catalyst for conversion of 2,4,6-tri-O-acetyl-d-glycal to 2,3-unsaturated O-glycosides. A wide range of alcohols including naturally bioactive compounds could be coupled with the glycal to give the desired products in good to excellent yields and with high levels of α-selectivity.