Alkylating ability of carbohydrate oxetanes: Practical synthesis of bolaform skeleton derivatives
Abstract
The alkylating ability of the oxetane ring in the carbohydrate structure was investigated and a flexible method for the construction of a bolaform amphiplile skeleton with xylose as the polar head is proposed. The method is based on oxetane ring opening in the easily accessible 3,5-anhydro-1,2-O-cyclohexylidenexylofuranose (1). One-step nitrogen alkylation in terminal diamines with 1 gave the basic cationic bolaform skeleton with xylose as potential polar head and a deliberately chosen length of the non-polar spacer. Under similar experimental conditions, but with an appropriate mole ratio of the alkylating agent, the alkylation reaction provide for selective monoalkylation of the diamines. Successful alkylation in the xanthine series (theophylline) was also achieved with 1, giving a new 5-deoxy-5-(1,2,3,6-tetrahydro-1,3-dimethyl- 2,6-dioxo-7H-purin-7-yl)-alpha-D-xylofuranose derivative.
Keywords:
bolaform skeleton / oxetane ring / alkylation / ring openingSource:
Journal of the Serbian Chemical Society, 2015, 80, 10, 1273-Publisher:
- Srpsko hemijsko društvo, Beograd
DOI: 10.2298/JSC150224033H
ISSN: 0352-5139
WoS: 000364206300004
Scopus: 2-s2.0-84957536365
Collections
Institution/Community
Fakultet veterinarske medicineTY - JOUR AU - Hadzić, Pavle A. AU - Popsavin, Mirjana M. AU - Borozan, Sunčica PY - 2015 UR - https://vet-erinar.vet.bg.ac.rs/handle/123456789/1192 AB - The alkylating ability of the oxetane ring in the carbohydrate structure was investigated and a flexible method for the construction of a bolaform amphiplile skeleton with xylose as the polar head is proposed. The method is based on oxetane ring opening in the easily accessible 3,5-anhydro-1,2-O-cyclohexylidenexylofuranose (1). One-step nitrogen alkylation in terminal diamines with 1 gave the basic cationic bolaform skeleton with xylose as potential polar head and a deliberately chosen length of the non-polar spacer. Under similar experimental conditions, but with an appropriate mole ratio of the alkylating agent, the alkylation reaction provide for selective monoalkylation of the diamines. Successful alkylation in the xanthine series (theophylline) was also achieved with 1, giving a new 5-deoxy-5-(1,2,3,6-tetrahydro-1,3-dimethyl- 2,6-dioxo-7H-purin-7-yl)-alpha-D-xylofuranose derivative. PB - Srpsko hemijsko društvo, Beograd T2 - Journal of the Serbian Chemical Society T1 - Alkylating ability of carbohydrate oxetanes: Practical synthesis of bolaform skeleton derivatives VL - 80 IS - 10 SP - 1273 DO - 10.2298/JSC150224033H ER -
@article{ author = "Hadzić, Pavle A. and Popsavin, Mirjana M. and Borozan, Sunčica", year = "2015", abstract = "The alkylating ability of the oxetane ring in the carbohydrate structure was investigated and a flexible method for the construction of a bolaform amphiplile skeleton with xylose as the polar head is proposed. The method is based on oxetane ring opening in the easily accessible 3,5-anhydro-1,2-O-cyclohexylidenexylofuranose (1). One-step nitrogen alkylation in terminal diamines with 1 gave the basic cationic bolaform skeleton with xylose as potential polar head and a deliberately chosen length of the non-polar spacer. Under similar experimental conditions, but with an appropriate mole ratio of the alkylating agent, the alkylation reaction provide for selective monoalkylation of the diamines. Successful alkylation in the xanthine series (theophylline) was also achieved with 1, giving a new 5-deoxy-5-(1,2,3,6-tetrahydro-1,3-dimethyl- 2,6-dioxo-7H-purin-7-yl)-alpha-D-xylofuranose derivative.", publisher = "Srpsko hemijsko društvo, Beograd", journal = "Journal of the Serbian Chemical Society", title = "Alkylating ability of carbohydrate oxetanes: Practical synthesis of bolaform skeleton derivatives", volume = "80", number = "10", pages = "1273", doi = "10.2298/JSC150224033H" }
Hadzić, P. A., Popsavin, M. M.,& Borozan, S.. (2015). Alkylating ability of carbohydrate oxetanes: Practical synthesis of bolaform skeleton derivatives. in Journal of the Serbian Chemical Society Srpsko hemijsko društvo, Beograd., 80(10), 1273. https://doi.org/10.2298/JSC150224033H
Hadzić PA, Popsavin MM, Borozan S. Alkylating ability of carbohydrate oxetanes: Practical synthesis of bolaform skeleton derivatives. in Journal of the Serbian Chemical Society. 2015;80(10):1273. doi:10.2298/JSC150224033H .
Hadzić, Pavle A., Popsavin, Mirjana M., Borozan, Sunčica, "Alkylating ability of carbohydrate oxetanes: Practical synthesis of bolaform skeleton derivatives" in Journal of the Serbian Chemical Society, 80, no. 10 (2015):1273, https://doi.org/10.2298/JSC150224033H . .