Anomer-specificity in the degradation reaction of D-glucopyranuronic acid tetraacetate leading to comanic acid in the acetic anhydride-base system

✍ Scribed by Kiyohiko Tajima

• Publisher: Elsevier Science
• Year: 1986
• Tongue: French
• Weight: 273 KB
• Volume: 27
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)85407-6

✦ Synopsis

Degradation reaction of 1,2,3,4-tetra-&acetyl-q_glucopyranuranic acid(Z) was investigated in acetic anhydride-base system. And it was made clear that the second B-elimination in the degradation reaction of 2 to comanic acid(4) occurred advantageously in 8-anomer of 2 to afford 4 selectively under milder condition. We have already reported that the degradation of a-Dgalactopyranuronic acid or its tetraacetate in acetic anhydride-base system proceeded by a combination of elimination reaction and recyclization reaction to give the 4,5-unsaturated compound(3_a), 3-acetoxy-6-(diacetoxymethyl)-2H-pyran-2-one(z) or comanic acid(!), and the directions of the degradation reactions could be controlled by suitable combinations