Samarium(II) iodide mediated intramolecular homolytic substitution at selenium: Preparation of 5-seleno-D-pentopyranose sugars from common pentose starting materials

✍ Scribed by Carl H. Schiesser; Shi-Long Zheng

• Book ID: 104261773
• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 203 KB
• Volume: 40
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(99)00990-9

✦ Synopsis

Treatment of 2,

3,

with samarium(II) iodide in THF affords 2,3,4-tri-O-benzyl-5-deoxy-5-seleno-D-ribopyranose ~10) in 50% isolated yield in a process most likely involving intramolecular homolytic substitution at the selenium atom. In a similar fashion, 2,3,4-tri-O-benzyl-5-deoxy-5-seleno-D-xylopyranose ( 16) and 2,3,4-tri-O-benzyl-5-deoxy-5seleno-D-arabanopyranose (17) were prepared from analogous precursors in 21 and 12% yields respectively.