Ballardie F W, Capon B, Dearie W M, Foster R L
Carbohydr Res. 1976 Jul;49:79-92. doi: 10.1016/s0008-6215(00)83127-4.
Kinetic measurements suggest that neighbouring acetamido-group participation occurs in the spontaneous hydrolysis and methanolysis of o-carboxyphenyl 2-acetamido-2-deoxy-beta-D-glucopyranoside and in the spontaneous hydrolysis of 2,4-dinitrophenyl 2-acetamido-2-deoxy-beta-D-glucopyranoside and 2-acetamido-2-deoxy-beta-D-glycopyranosyl fluoride. The methanolyses of these compounds proceed with predominant retention of configuration which is also consistent with neighbouring acetamido-group participation. The oxazoline intermediate which would arise from such a process was detected during methanolysis of 2-acetamido-2-deoxy-beta-D-glucopyranosyl fluoride in the presence of bases by n.m.r., i.r., and u.v. spectroscopy. Attempts to isolate the oxazoline were unsuccessful.
动力学测量表明，在邻羧基苯基2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖苷的自发水解和甲醇解过程中，以及在2,4-二硝基苯基2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖苷和2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖基氟化物的自发水解过程中，存在相邻乙酰氨基基团的参与。这些化合物的甲醇解反应主要以构型保持为主，这也与相邻乙酰氨基基团的参与一致。在碱存在下，通过核磁共振、红外光谱和紫外光谱在2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖基氟化物的甲醇解过程中检测到了由该过程产生的恶唑啉中间体。分离恶唑啉的尝试未成功。
