Premium
C ‐Glycosyl Styrene Type Compounds by Pd‐Catalyzed Cross‐Coupling Reactions of Anhydro‐Aldose Tosylhydrazones with Benzyl Bromides
Author(s) -
Kaszás Tímea,
Tóth Marietta,
Langer Peter,
Somsák László
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201801059
Subject(s) - chemistry , styrene , aldose , glycosyl , catalysis , palladium , coupling reaction , sequence (biology) , organic chemistry , stereochemistry , glycoside , copolymer , biochemistry , polymer
C ‐Glycopyranosyl styrene type compounds are valuable synthetic intermediates whose syntheses are known in rather lengthy procedures. Herein palladium‐catalyzed cross‐couplings of O ‐peracylated 2,6‐anhydro‐aldose tosylhydrazones with benzyl bromides were studied under thermic conditions in the presence of LiO t Bu. The reactions gave the corresponding C ‐glycopyranosyl styrenes in up to 59% yields. The transformations represent a new, short synthetic sequence to get this type of glycomimetic compounds in 4–5 steps from a free aldose.