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Citation: TIAN Li-Li, LI Zhong-Jun, LI Hui. Synthesis of Deoxynojirimycin(DNJ)[J]. Chinese Journal of Applied Chemistry, ;2004, 21(1): 12-15. shu

Synthesis of Deoxynojirimycin(DNJ)

1.
Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100083

Corresponding author: LI Hui,
Received Date: 8 April 2003
Available Online: 9 July 2003
Fund Project: 国家自然科学基金资助项目(30000031) (30000031)

A facile synthesis of 1-dexoynojirimycin(DNJ), an important glycosidase inhibitor, using L-sorbose as the starting material. The hydroxy groups at C-2,3, of L-sorbose was selectively protected and an azide group was introduced at C-6, affording the key intermediate 6-deoxy-6-amino-L-sorbofuranose hydrochloride via catalytic hydrogenation and hydrolysis. The intermediate was converted into the target compound 1-deoxynojirimycin hydrochloride in a hydrogenation procedure, an epimer of DNJ being also generated but difficult to separate from the mixture in conventional ways. By means of benzyloxycarbonylation, N-benzyloxycarbonyl-1-deoxynojirimycin was isolated from the mixture.
- deoxynojirimycin(DNJ),
- glycosidase,
- synthesis,
- isomer seperation
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