Facile Synthesis of (2R,3S)-2-Benzyloxy-3-hydroxybutyrolactone |
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Authors: | Amer El-Batta |
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Institution: | 1. Department of Chemistry , King Fahd University of Petroleum and Minerals , Dhahran , Saudi Arabia aelbatta@kfupm.edu.sa |
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Abstract: | The heterocyclic diols derived from L-dimethyl tartrate are important chiral synthons in organic synthesis. In particular, L-threosolactone and L-threosolactam structures are versatile precursors for the synthesis of biologically active molecules. Structurally, these functionalized five-membered rings contain two hydroxyl groups with R and S stereochemistry on C-2 and C-3 respectively. The preparation of (2R,3S)-2-benzyloxy-3-hydroxybutyrolactone (3) and of its derivatives, drawing upon L-dimethyl tartrate as an inexpensive chiral starting material, is described. The presented synthetic procedures are easy and effective for preparing L-threoso analogs. This protocol is also a better alternative in a large scale setup. All structures 3–6 and 8 are characterized using 1H and 13C NMR spectroscopy. |
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Keywords: | Butyrolactone chiral L-threosolactone organic synthesis tartrate |
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