Determination of the substituent distribution in O-sulfonylbutyl-(1-->4)-glucans.
A method has been developed to determine the distribution of substituents in the glucose units of sulfonylbutylethers of cyclomaltoheptaose (beta-cyclodextrin). This method involves hydrolysis of the glucosidic linkages, permethylation, formation of sulfonylchlorides and subsequent transformation to the permethylated sulfonylfluoride derivatives. The latter were thermostable and could be analyzed by GLC and identified by EI and CIMS. For confirmation, the 2-, 3-, and 6-O-substituted standard compounds were independently synthesized and characterized by NMR and GLC-MS.
Rogmann
N
N
Universität Hamburg, Institut für Organische Chemie, Germany.
Jones
P
P
Mischnick
P
P
D000476:Alkanesulfonates / Q000737:chemistry; D002236:Carbohydrate Conformation; D002849:Chromatography, Gas; D003505:Cyclodextrins / Q000737:chemistry*; D004355:Drug Stability; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D005936:Glucans / Q000138:chemical synthesis / Q000737:chemistry*; D007202:Indicators and Reagents; D013058:Mass Spectrometry; D013451:Sulfonic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D013816:Thermodynamics; D047392:beta-Cyclodextrins
D000476:Alkanesulfonates; D003505:Cyclodextrins; D004987:Ethers; D005936:Glucans; D007202:Indicators and Reagents; D013451:Sulfonic Acids; D047392:beta-Cyclodextrins; C000335:butanesultone; C031215:betadex