ISSN:
0947-3440
Keywords:
Nucleoside derivatives
;
Aminonucleosides
;
Isothiocyanates of nucleosides
;
Dideoxynucleosides
;
Labelling of nucleosides
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
3′-Deoxy-3′-isothiocyanatothymidine (4), 3′,5′-protected 2′-deoxy-2′-isothiocyanatouridine (8), and 2′,3′-dideoxy-2′-isothiocyanatouridine (14), respectively, have been prepared from the corresponding 2′- or 3′-amino derivatives. SnCl2, Bu3SnH, and dithiothreitol were employed to reduce the 2′- or 3′-azido derivatives to give the aminonucleosides which served as starting materials for the thiocarbonylation. Thiocarbonylation, by either a mixture of carbon disulfide and mercuric oxide or N,N′-thiocarbonyldiimidazole, leads directly to the target molecules in high yields. Furthermore, the direct transformation of azidonucleosides into the corresponding isothiocyanto derivatives via treatment of phosphanimine nucleosides with CS2 is described. Th activity of the isothiocyanate group is used for covalent coupling of different linking molecules or dyes to the carbohydrate moiety of the nucleosides.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199719970322
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