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Novel Stereoelectronic Behavior of Bicyclic Glycosyl Donors: Application to the Synthesis of Both 2‐Deoxy‐α‐ and ‐β‐Glycosides
Author(s) -
Dios Angeles,
Nativi Cristina,
Capozzi Giuseppe,
Franck Richard W.
Publication year - 1999
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/(sici)1099-0690(199908)1999:8<1869::aid-ejoc1869>3.0.co;2-a
Subject(s) - chemistry , glycosyl , glycosylation , glycosyl donor , anomer , glycoside , stereochemistry , bicyclic molecule , biochemistry
Two pairs of novel stereoisomeric, cyclic glycosyl donors exhibit different behaviors in glycosylation processes. In the pair of α‐ gluco ( 1 ) and β‐ manno ( 2 ), the former exhibits reversability with its glycoside product whereas the latter does not. In the α‐ gluco ( 3 ) and β‐ manno ( 4 ) set, the former undergoes glycosyl transfer via an isolable intermediate whereas the latter does not. The differing anomeric effects exerted in the ground states are proposed as the force which explains the differences in behavior.