Facile Synthesis of (2R,3S)-2-Benzyloxy-3-hydroxybutyrolactone

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.

GRAPHICAL ABSTRACT

Keywords:

• Butyrolactone
• chiral
• L-threosolactone
• organic
• synthesis
• tartrate

ACKNOWLEDGMENTS

The author acknowledges the support provided by the Deanship of Scientific Research (DSR) at King Fahd University of Petroleum and Minerals (KFUPM) for funding this work through Project No. IN101005. The support of the Department of Chemistry at KFUPM is also highly appreciated.