Abstract

Opening of the 1,6-anhydro bridge in levoglucosenone by the action of acetic anhydride in the presence of ZnCl₂ afforded diastereoisomeric 1,6-di-O-acetyl-3,4-dideoxy-α/β-D-glycero-hex-3-enopyranos-2-uloses, and alcoholysis of the resulting diacetates in methanol, ethanol, and propan-2-ol in the presence of p-toluenesulfonic acid, camphor-10-sulfonic acid, ZnCl₂, and HCl was studied. Their methanolysis in the presence of CSA gave methyl 3,4-dideoxy-α/β-D-glycero-hex-3-enopyranosid-2-uloses that are precursors to purpurosamine C and (+)-frontalin.

中文翻译：

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从左旋葡萄糖酮合成 Methyl-3,4-Dideoxy-α(β)-D-glycero-hex-3-enopyranosiduloses

摘要

在 ZnCl ₂存在下通过乙酸酐的作用打开左旋葡萄糖酮中的 1,6-脱水桥，得到非对映异构体 1,6-二-O-乙酰基-3,4-双脱氧-α/β-D-甘油-hex在对甲苯磺酸、樟脑-10-磺酸、ZnCl ₂和 HCl存在下，研究了 -3-enopyranos-2-uloses 和所得二乙酸酯在甲醇、乙醇和丙-2-醇中的醇解。它们在 CSA 存在下的甲醇分解产生甲基 3,4-二脱氧-α/β-D-甘油-hex-3-enopyranosid-2-uloses，它是 purpurosamine C 和 (+)-frontalin 的前体。