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)

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

Journal Name: Letters in Organic Chemistry

Volume 10 , Issue 7 , 2013

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.

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Article Details

VOLUME: 10
ISSUE: 7
Year: 2013
Page: [538 - 540]
Pages: 3
DOI: 10.2174/15701786113109990004
Price: $58

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