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Preparation of 5-Selenopentopyranose Sugars from Pentose Starting Materials by Samarium(II) Iodide or (Phenylseleno)formate Mediated Ring Closures

โœ Scribed by Mathew A. Lucas; Oanh T.K. Nguyen; Carl H. Schiesser; Shi-Long Zheng


Book ID
108370822
Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
122 KB
Volume
56
Category
Article
ISSN
0040-4020

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Samarium(II) iodide mediated intramolecu
โœ Carl H. Schiesser; Shi-Long Zheng ๐Ÿ“‚ Article ๐Ÿ“… 1999 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 203 KB

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-xylo