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Synthesis of carboxyl cellulose sulfates with regioselective sulfation and regiospecific oxidation using cellulose trifluoroacetate as intermediates |
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| Authors: | Kai Zhang Steffen Fischer Andreas Geissler Erica Brendler Kathrin Gebauer |
| Affiliation: | 1. Institute of Macromolecular Chemistry and Paper Chemistry, Technische Universit?t Darmstadt, Petersenstr. 22, 64287, Darmstadt, Germany 2. Institute of Plant and Wood Chemistry, Dresden University of Technology, Pienner Str. 19, 01737, Tharandt, Germany 3. Institute of Analytical Chemistry, Freiberg University of Mining and Technology, Leipziger Str. 29, 09599, Freiberg, Germany 4. Institute of Power Engineering, Dresden University of Technology, Helmholtzstr. 10, 01069, Dresden, Germany |
| Abstract: | Synthesis of cellulose sulfates (CSs) and carboxyl cellulose sulfates (COCSs) with regioselectively or regiospecifically distributed functional groups within anhydroglucose units was reported. CS with regioselectively distributed sulfate groups at 2,3-O- or 2,6-O-position were homogeneously synthesized and cellulose trifluoroacetate (CTFA) was used as intermediates. The trifluoroacetyl groups were detected primarily at 6-O-position and their distributions could be altered by changing the amount of trifluoroacetyl anhydride (TFAA). Various sulfating agents were used for further homogeneous sulfation of CTFA. The total degree of sulfation (DSS) and the distribution of sulfate groups within the repeating units were affected by the amount of TFAA, the type and amount of sulfating agents. Subsequent homogenous 4-acetamide-TEMPO or TEMPO-mediated oxidation of CS led to COCS with carboxyl groups regiospecifically distributed at C6 position, which may be interesting structural mimics for natural occurring heparin. |
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