Improved synthesis of 2,5-anhydro-d-allononitrile

✍ Scribed by Hassan S. El Khadem; Joshua Kawai

• Publisher: Elsevier Science
• Year: 1983
• Tongue: English
• Weight: 539 KB
• Volume: 115
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(83)88141-5

✦ Synopsis

Two types of mixed ester of j&D-ribofuranose were synthesized. The first had the same groups attached to O-l, 2, and 3, and the second had the same groups attached to O-2,3, and 5. The three esters obtained in the highest yields, starting from D-ribose, were then converted into the halides and nitriles. Of the esters studied, the best suited for conversion into the nitrile was l-O-acetyl-2,3,5-tri-O-p-toluyl+Dribofuranose, which afforded 2,5-anhydro-3,4,6-tri-O-p-toluyl-D-allononitrile in 60% yield. ' (14 and IS) are obtained in poor yield (9 and 14 '$4, respectively) from D-ribose, and are therefore not useful starting-materials.