NaHSO₄ supported on silica gel: an alternative catalyst for Ferrier rearrangement of glycals

NaHSO₄ supported on silica gel catalyses the Ferrier rearrangement reaction of 3,4,6-tri-O-acetyl-d-glucal with alcohols and thiols to give the corresponding 2,3-unsaturated glycosides in high anomeric selectivity and good to excellent yield in short reaction time.

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Bibliographic Details
Published inCarbohydrate research Vol. 346; no. 16; pp. 2528 - 2532
Main Authors Kinfe, Henok H, Mebrahtu, Fanuel M, Sithole, Khuphukile
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 29.11.2011
Elsevier
Subjects
alcohols
Biochemistry & Molecular Biology
catalysts
Chemistry
Chemistry, Applied
Chemistry, Organic
glycosides
Life Sciences & Biomedicine
Physical Sciences
Science & Technology
silica gel
thiols
MILD
NaHSO4
FACILE SYNTHESIS
Silica gel
Glycoside
GLYCOSYLATION
EPOXIDATION-ALCOHOLYSIS
Ferrier rearrangement
STEREOSELECTIVE IODOACETOXYLATION
EFFICIENT
Glucal
C-GLYCOSIDATION
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Summary:NaHSO₄ supported on silica gel catalyses the Ferrier rearrangement reaction of 3,4,6-tri-O-acetyl-d-glucal with alcohols and thiols to give the corresponding 2,3-unsaturated glycosides in high anomeric selectivity and good to excellent yield in short reaction time.
Bibliography:http://dx.doi.org/10.1016/j.carres.2011.08.023
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2011.08.023