Beilstein J. Org. Chem.2010,6, No. 20, doi:10.3762/bjoc.6.20
pseudooligosaccharides having cyanamide, urea and thiourea-linkages via the Staudingerreaction have been reported [69][70].
In our group, the carbodiimide approach was used to prepare calystegine B2 analogues with the urea-linked disaccharide structure (Figure 15). These compounds, however, did not show inhibitory
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Graphical Abstract
Figure 1:
Schematic representation of sugar aminoacids (SAAs) and (pseudo)amide oligosaccharide mimetics.
Beilstein J. Org. Chem.2006,2, No. 23, doi:10.1186/1860-5397-2-23
synthesised from 5'-tosylated intermediates, [36] whilst 3'-azido-3'-deoxythymidine 6 was prepared via a Mitsunobu type reaction. [37]
Staudingerreaction of azidonucleosides 3–6 with triphenylphosphine led to iminophosphorane intermediates 7–10, which reacted subsequently with active esters of coumarin-4