Abstract
Protections of hydroxyl groups of chitin by triphenylmethylation and benzylation were studied in detail to synthesize precursors for efficient regioselective chemical modifications in organic solvents. The reactions of squid β-chitin with triphenylmethyl chloride and benzyl chloride proceeded much more facilely than those of shrimp α-chitin, and quantitative 6-O-triphenylmethylation and 3,6-O-dibenzylation of β-chitin were accomplished in the presence of dimethylaminopyridine and sodium hydride, respectively, in simple one-step reactions. The resulting protected derivatives exhibited high affinity for organic solvents and would allow modification reactions under homogeneous or almost homogeneous conditions in suitable solvents.
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