Large laboratory scale synthesis of (2S,3S)-2-(4-methoxybenzyloxy)-3,4-O-(3-pentylidene)-1,3,4-butantriol, a versatile chiral building block in natural product synthesis

(2S, 3S)-2-(4-Methoxybenzyloxy)-3, 4-O-(3-pentylidene)-1, 3, 4-butanetriol (3), a versatile chiral building block for an essential structural unit of complex natural products, was synthesized starting from dimethyl L-(+)-tartrate (5) on both a small scale and a large scale in good yield.