Citation: Tian-Yu Xia, Yang-Bing Li, Zhao-Jun Yin, Xiang-Bao Meng, Shu-Chun Li, Zhong-Jun Li. Synthesis of L-glucose and L-galactose derivatives from D-sugars[J]. Chinese Chemical Letters, ;2014, 25(9): 1220-1224. doi: 10.1016/j.cclet.2014.06.007 shu

Synthesis of L-glucose and L-galactose derivatives from D-sugars

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The State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Science, Peking University, Beijing 100191, China

Corresponding author: Shu-Chun Li, Zhong-Jun Li,
Received Date: 15 April 2014
Available Online: 3 June 2014
Fund Project: This research was supported by the National Basic Research Program of China (973 Program, No. 2012CB822100) (973 Program, No. 2012CB822100) the National Key Technology R&D Program "New Drug Innovation" of China (No. 2012ZX09502001-001) (No. 2012ZX09502001-001)

An efficient route to prepare L-glucose and L-galactose is described. The L-sugars are achieved by using the strategy of switching the functional groups at C1 and C5 of D-glucose and D-mannose. The oxidation and reduction of the silyl enol ether at C1 and the lead(IV) tetraacetate mediated oxidative decarboxylation at C5 are the key steps. L-Glucose and L-galactose are prepared in a convenient and inexpensive way.
- Carbohydrates,
- L-Hexoses,
- Head-to-tail inversions,
- Oxidation,
- Decarboxylation,
- One-pot procedure
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