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Synthesis of an L ‐Fucose‐Derived Cyclic Nitrone and its Conversion to α ‐ L ‐Fucosidase Inhibitors
Author(s) -
Peer Andreas,
Vasella Andrea
Publication year - 1999
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/(sici)1522-2675(19990707)82:7<1044::aid-hlca1044>3.0.co;2-3
Subject(s) - chemistry , fucosidase , nitrone , hydroxylamine , yield (engineering) , intramolecular force , imidazole , alkylation , stereochemistry , medicinal chemistry , fucose , organic chemistry , cycloaddition , catalysis , galactose , materials science , metallurgy
The L ‐ fuco ‐nitrone 1 has been synthesized from allyl 4,6‐ O ‐benzylidene‐ α ‐ D ‐glucopyranoside ( 4 ) in 11 steps and an overall yield of 18%. The key step is the intramolecular alkylation of an intermediary 1,1‐bis(hydroxylamine) derived from the tosyloxy oximes ( E / Z )‐ 2 . The nitrone 1 has been transformed into the diamine 30 , the indolizidines 39 and 40 , the indolizidinones 34 and 35 , and the imidazole 44 , all inhibiting bovine epididymis α ‐ L ‐fucosidase with IC 50 values between 105 n M and 240 μ M .