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2‐Acetamido‐2‐deoxy‐ l ‐iminosugar C ‐Alkyl and C ‐Aryl Glycosides: Synthesis and Glycosidase Inhibition
Author(s) -
Fontelle Nathalie,
Yamamoto Arisa,
Arda Ana,
JiménezBarbero Jesús,
Kato Atsushi,
Désiré Jérôme,
Blériot Yves
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800678
Subject(s) - iminosugar , chemistry , substituent , stereochemistry , glycoside hydrolase , aryl , alkyl , alkylation , ring (chemistry) , glycoside , hydrolysis , enzyme , organic chemistry , catalysis
The synthesis of a series of six‐membered 2‐acetamido l ‐iminosugar C ‐alkyl and C ‐aryl glycosides is reported. A diastereoselective sugar‐ring enlargement/ C ‐alkylation (or arylation) /ring‐contraction sequence applied to d ‐ gluco ‐ and d ‐ manno ‐configured 2‐acetamido azidolactols provides new l ‐iminosugar C ‐glycosides. The 1,2‐ trans stereocontrolled introduction of the pseudoanomeric substituent in these heterocycles strongly suggests a NHAc neighbouring‐group participation. In their deprotected form, the nine iminosugars exhibit moderate hexosaminidases and β‐glucuronidase inhibition.