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Letters in Organic Chemistry

Author(s): Qi He, Zhouyu Wang, Xianggui Chen, Zhenju Jiang, Wensi Ai and Dehong Jiang

DOI: 10.2174/15701786113109990004

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An Efficient Way to the Synthesis of 2-Deoxy-2-[(7-nitro-2,1,3- benzoxadiazol-4-yl)amino]-β-D-glucopyranose (2-NBDG) via 7-Nitro-2,1,3- benzoxadiazol-4-yl Chloride (NBD-Cl)

Page: [538 - 540] Pages: 3

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Abstract

The fluorescent D-glucose derivative, 2-deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-β-Dglucopyranose (2-NBDG) is synthesized by reacting D-glucosamine with inexpensive 7-nitro-2,1,3-benzoxadiazol-4-yl chloride (NBD-Cl). A series of reaction conditions such as reaction time, bases, the loading of bases, solvents and reaction temperature has been investigated. The yield of 2-NBDG can be enhanced to 83.0% under the optimal reaction conditions. Meanwhile, a gram-scale synthesis of 2-NBDG was also realized with 80.0% isolated yield.

Keywords: Fluorescent reagent, D-glucose derivative, NBD-Cl, synthesis.