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Novel Stereoelectronic Behavior of Bicyclic Glycosyl Donors: Application to the Synthesis of Both 2-Deoxy-α- and -β-Glycosides (1999)

Dios, Angeles ; Nativi, Cristina ; Capozzi, Giuseppe ; [et al.]

Weinheim : Wiley-Blackwell

Liebigs Annalen 1999 (1999), S. 1869-1874

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ISSN: 1434-193X

Keywords: Carbohydrates ; Heterocycles ; Electrostatic interactions ; Glycosylation ; Glycosides ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: 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.

Type of Medium: Electronic Resource

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