C ‐Glycosyl Styrene Type Compounds by Pd‐Catalyzed Cross‐Coupling Reactions of Anhydro‐Aldose Tosylhydrazones with Benzyl Bromides | Zendy

Kaszás Tímea | Zendy; Tóth Marietta | Zendy; Langer Peter | Zendy; Somsák László | Zendy

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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 , glycosyl , styrene , aldose , catalysis , coupling reaction , sequence (biology) , palladium , stereochemistry , organic chemistry , 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.

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