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Halogenation and anomerization of glycopyranoside by TESH /bromine and BHQ /bromine
Author(s) -
Xu Lai,
Luo ChinHung,
Chen ChienSheng
Publication year - 2021
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.202000150
Subject(s) - chemistry , halogenation , bromine , glycosidic bond , isopropyl , halogen , glycosyl , glycoside , halide , medicinal chemistry , solvent , organic chemistry , alkyl , enzyme
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.