Open AccessAlkylating ability of carbohydrate oxetanes: Practical synthesis of bolaform skeleton derivative
Author(s) -
A Pavle Hadzic,
Mirjana Popsavin,
Sunčica Borozan
Publication year - 2015
Publication title -
journal of the serbian chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.227
H-Index - 45
eISSN - 1820-7421
pISSN - 0352-5139
DOI - 10.2298/jsc150224033h
Subject(s) - oxetane , alkylation , chemistry , xylose , cationic polymerization , ring (chemistry) , carbohydrate , derivative (finance) , formaldehyde , polar , organic chemistry , combinatorial chemistry , physics , astronomy , fermentation , financial economics , economics , catalysis
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