Alkylating ability of carbohydrate oxetanes: Practical synthesis of bolaform skeleton derivative

• Main Authors: Hadžić Pavle A., Popsavin Mirjana M., Borozan Sunčica Z.
• Format: Article
• Language: English
• Published: Serbian Chemical Society 2015-01-01
• Series: Journal of the Serbian Chemical Society
• Subjects: bolaform skeleton; oxetane ring; alkylation; ring opening
• Online Access: http://www.doiserbia.nb.rs/img/doi/0352-5139/2015/0352-51391500033H.pdf
• ISSN: 0352-5139; 1820-7421

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.