Glycopyranosyl isothiocyanates

Application of this methodology allowed the preparation of several multivalent neoglycoconjugates bearing some glycopyranoso[ l,2-d]thiazoline motifs when reaction was carried out between the 2-iodo-glycopyranosyl isothiocyanate and a symmetric polyamine [94]. As an example, the preparation of compounds 77 and 78 is remarkable, derived from 71 and a calix[4]arene or a triamine, respectively (Fig. 2). 

Glycopyranosyl isothiocyanates 103 were obtained by the method described by Camarasa and co-workers [133], involving treatment of protected glycopyranosyl bromides with potassium thiocyanate imder phase-transfer conditions (Scheme 25). Diazadienium iodide 114 was prepared by sulfhydra-tion of commercially available 3-dimethylaminoacrylonitrile 112, followed by methylation on the sulfm atom of thioamide 113 (Scheme 25). 

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