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Halogenation and anomerization of glycopyranoside by TESH/bromine and BHQ/bromine
Journal of the Chinese Chemical Society ( IF 1.8 ) Pub Date : 2020-07-06 , DOI: 10.1002/jccs.202000150
Lai Xu, Chin‐Hung Luo, Chien‐Sheng Chen

Treatment of peracetylated glycosides and β‐isopropyl glycosides with halogen in the presence of TESH and BHQ has been found to result in the halogenation and the anomerization, respectively. Peracetylatedglycosides treaded with I2/TESH or Br2/TESH leading tothe formation of corresponding glycosyl halides, and b‐isopropyl glycosidesreacted with Br2/BHQ resulting in the formation of a‐glycosides. The anomerizationof glycosidic bond was considered to be catalyzed by in situ formation of hydrogenbromide from the mixing of Br2/BHQ.

中文翻译:

TESH /溴和BHQ /溴对吡喃葡萄糖苷的卤化和异构化作用

已经发现在TESH和BHQ存在下用卤素处理过乙酰化的糖苷和β-异丙基糖苷分别导致卤化和异构化。过乙酰化的糖苷与I2 / TESH或Br2 / TESH结合使用会导致形成相应的糖基卤化物,而b-异丙基糖苷与Br2 / BHQ反应会导致a-糖苷的形成。糖苷键的异构化被认为是由Br2 / BHQ的混合原位形成溴化氢所催化的。
更新日期:2020-07-06
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