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KMID : 0525720090140020101
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Journal of Chitin and Chitosan
2009 Volume.14 No. 2 p.101 ~ p.106
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A Synthesis of N-(2-Deoxy-β-D-glucopyranosyl)-N`-(4-aminomethyl-2-imino-1,3-thiazoline) urea Derivatives
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Han Hoh-Gyu
Mah He-Duck
Shin Dong-Yun
Nam Kee-Dal
Han Min-Soo
Heo Jeong-hoe
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Abstract
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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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KEYWORD
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β-D-glucosamine, Isocyanate, Triphosgene, Thiazoline, Phthalimide
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