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- W2093736847 abstract "Chitosan (1) was prepared by basic hydrolysis of chitin of an average molecular weight of 70000 Da, 1H-NMR spectra indicating almost complete deacetylation. N-Phthaloylation of 1 yielded the known N-phthaloylchitosan (2), which was tritylated to provide 3a and methoxytritylated to 3b. Dephthaloylation of 3a with NH2NH2⋅H2O gave the 6-O-tritylated chitosan 4a. Similarly, 3b gave the 6-O-methoxytritylated 4b. CuSO4-Catalyzed diazo transfer to 4a yielded 95% of the azide 5a, and uncatalyzed diazo transfer to 4b gave 82% of azide 5b. Further treatment of 5a with CuSO4 produced 2-azido-2-deoxycellulose (7). Demethoxytritylation of 5b in HCOOH gave 2-azido-2-deoxy-3,6-di-O-formylcellulose (6), which was deformylated to 7. The 1,3-dipolar cycloaddition of 7 to a range of phenyl-, (phenyl)alkyl-, and alkyl-monosubstituted alkynes in DMSO in the presence of CuI gave the 1,2,3-triazoles 8–15 in high yields." @default.
- W2093736847 created "2016-06-24" @default.
- W2093736847 creator A5001180898 @default.
- W2093736847 creator A5031307879 @default.
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- W2093736847 creator A5056568607 @default.
- W2093736847 creator A5070811586 @default.
- W2093736847 creator A5075695962 @default.
- W2093736847 date "2008-04-01" @default.
- W2093736847 modified "2023-09-26" @default.
- W2093736847 title "2-Azido-2-deoxycellulose: Synthesis and 1,3-Dipolar Cycloaddition" @default.
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