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Glycosyl Glycerol Derivatives as Drug Carrier System. Stereoselective Synthesis of Epoxyalkyl N ‐Acyl‐β‐ D ‐glucopyranosides and Their Reactivity with Nucleophiles
Author(s) -
VegaPérez José M.,
Candela José I.,
Romero Isidora,
Blanco Eugenia,
IglesiasGuerra Fernando
Publication year - 2000
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 - 10.1002/1099-0690(200012)2000:23<3949::aid-ejoc3949>3.0.co;2-j
Subject(s) - chemistry , nucleophile , stereoselectivity , glycosyl , reactivity (psychology) , glycoside , anomer , organic chemistry , glycerol , stereochemistry , ring (chemistry) , catalysis , medicine , alternative medicine , pathology
The synthesis of alkenyl 2‐acylamino‐4,6‐ O ‐benzylidene‐2‐deoxy‐β‐ D ‐glucopyranosides from N ‐acetyl‐ D ‐glucosamine is described. The oxidation of alkenyl glycosides with m ‐CPBA gives the corresponding oxiranes in good yields, and with high stereoselectivity. Analogues of glycosyl glycerol derivatives, which can be used as drug carriers, were obtained by various ring‐opening reactions with different nitrogen, sulfur, and carbon nucleophiles.