An unusual reaction of 1,6-anhydroaldohexopyranose derivatives leading to glycals

✍ Scribed by Prakash Bhaté; Derek Horton

• Book ID: 102991084
• Publisher: Elsevier Science
• Year: 1985
• Tongue: English
• Weight: 742 KB
• Volume: 139
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(85)90019-9

✦ Synopsis

Treatment of a solution of the 2-O-(NJ+dimethylsulfamoyl) derivative 3 of the levoglucosenone-derived carbocycle 1 in liquid ammonia at -40 to -50" with sodium metal gave 73% of the glycal derivative 4 instead of the expected 2-deoxy derivative (2) of 1. Under the same conditions, the 2-O-(NJ-dimethylsulfamoyl)