PREPARATION OF TOSYLCHITINS AS PRECURSORS FOR FACILE CHEMICAL MODIFICATIONS OF CHITIN

Tosylation of chitin was accomplished by interfacial condensation to give tosylchitins expected to be useful as soluble and reactive precursors for chemical manipulations under mild conditions. The reaction was efficient even at low temperatures. Tosylation was quantitative with a 20-fold excess of tosyl chloride. Free amino groups in the tosylchitins were acylated to form well-defined structures. The tosylchitins with substitution degrees above 0.4 were soluble in common polar organic solvents. The resulting tosylchitins underwent efficiently reactions such as acetylation and iodination to fully acetylated tosylchitins and iodochitins. Iodochitins were more soluble than tosylchitins. Reduction of tosyl- and iodochitins with sodium borohydride led to deoxychitins.