A Synthesis of N-(2-Deoxy-β-D-glucopyranosyl)-N'-(4-aminomethyl-2-imino-1,3-thiazoline)urea Derivatives
- A Synthesis of N-(2-Deoxy-β-D-glucopyranosyl)-N'-(4-aminomethyl-2-imino-1,3-thiazoline)urea Derivatives
- 한호규; 마혜덕; 신동윤; 허정회; 한민수; 남기달
- β-D-glucosamine; isocyanate; triphosgene; thiazoline; Phthalimide
- Issue Date
- Journal of Chitin and Chitosan; 한국키틴키토산학회지
- VOL 14, NO 2, 101-106
- N-(2-Deoxy-β-D-glucopyranosyl)-N'-(4-aminomethyl-2-imino-1,3-thiazoline)urea derivatives 7 were synthesized from a reaction of
isocyanato-β-D-glucopyranose 6 with 4-aminomethyl-2-phenylimino-1,3-thiazoline derivatives 4. β-D-glucopyranosyl isothiocyanate
6 was obtained by a dehydrochlorination of β-D-glucosamine hydrogenchloride salt 5 followed by the reaction of triphogene,
which was unstable to isolate at room temperature. 4-Phthalimidyl-1,3-thiazoline dervitives derivatives 3 were prepared by a reaction
of α-bromoketophthalimide 1 with the corresponding N-methyl-N'-phenylthioureas 2, of which phthalimidyl protecting group
was deprotected by the treatment of methylamine to give the 4-aminomethyl-1,3-thiazolines 4. The effective methodology for synthesis
of β-D-glucopyranose derivatives in which ureido function was introduced at C-2 was presented from this study.
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