Stereoselective synthesis of various α-selenoglycosides using in situ production of α-selenolate anion

详细信息	查看全文 | 推荐本文 |

• 作者：Masahiro Nanami ; Hiromune Ando ; Yumiko Kawai ; Mamoru Koketsu ; Hideharu Ishihara
• 关键词：α ; -Selenoglycoside ; Pseudoglycoside ; Stereoselective synthesis
• 刊名：Tetrahedron Letters
• 出版年：2007
• 期刊代码：109_00404039
• 类别：ch
• 出版时间：12 February 2007
• 卷：48
• 期：7
• 页码：1113-1116
• 文件大小：164 K

摘要

A large variety of α-selenoglycosides, including alkyl and aryl selenoglycosides, selenoglycosyl amino acid and selenodisaccharide have been synthesized in a stereoselective manner. The key precursor of α-anomeric selenolate anion was designed as p-methylbenzoyl selenoglycoside, which was synthesized by the reaction of β-glycosyl chloride with potassium p-methylselenobenzoate. Upon the action of piperazine or methylhydrazine in the presence of Cs₂CO₃, the acyl selenoglycoside produced an anomeric selenolate anion, which reacted in situ with various electrophilic counterparts to yield α-selenoglycoside.