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Beilstein J. Org. Chem. 2013, 9, 135–146, doi:10.3762/bjoc.9.16
Graphical Abstract
Scheme 1: Structures of the different glycosylthiosemicarbazides.
Scheme 2: Glycosylations of oxadiazolinethione.
Scheme 3: Synthesis of glycosylthiosemicarbazides by solvolysis.
Scheme 4: Solvolysis of glycosylsulfanyloxadiazoles.
Scheme 5: Benzylation of the S- and N-glycosides 5–10.
Scheme 6: Aminolysis of benzylated indolyl-3-N-(glucosyl)- and (galactosyl)oxadiazolinethiones.
Figure 1: ORTEP representation of 23.
Figure 2: Packing diagram of 23.
Figure 3: ORTEP representation of 29.
Figure 4: Packing diagram of 29.
Figure 5: ORTEP representation of 30.
Figure 6: Packing diagram of 30.