Alkylating ability of carbohydrate oxetanes: Practical synthesis of bolaform skeleton derivative
| Autor: | Hadžić Pavle A., Popsavin Mirjana M., Borozan Sunčica Z. |
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| Jazyk: | angličtina |
| Rok vydání: | 2015 |
| Předmět: | |
| Zdroj: | Journal of the Serbian Chemical Society, Vol 80, Iss 10, Pp 1273-1278 (2015) |
| Druh dokumentu: | article |
| ISSN: | 0352-5139 1820-7421 |
| DOI: | 10.2298/JSC150224033H |
| Popis: | Alkylating ability of oxetane ring in carbohydrate structure was investigated and flexible method for bolaform amphiplile skeleton construction with xylose as polar heads is proposed. The method is based on oxetane ring opening in easily accessible 3,5-anhydro-1,2-O-cyclohexylidenexylofuranose (1). One step nitrogen alkylation in terminal diamines with 1 gave basic cationic bolaform skeleton with xylose as potential polar heads and deliberately chosen length of non polar spacer. Under similar experimental conditions, but with appropriate molar ratio of alkylating agent, alkylation reaction provide for selective monoalkylation of diamines. Successful alkylation in xanthine series (theophylline) was also achieved with 1, giving a new 5-deoxy-5-(7´-theophyllineamino)-α-D-xylofuranose derivative. |
| Databáze: | Directory of Open Access Journals |
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