A concise thiazole mediated synthesis of L-(-)-rhodinose from (S)-ethyl lactate. The thiazole route to deo

2-Lithiothiazole (2-LTT) (1a) and 2-thiazolylmethylene-triphenylphosphorane (2-TMP) (1b) are employed as aldehyde equivalents in a new concise synthesis of 4-O-tert-butyldimethylsilyl L-(-)-rhodinose (2b) from (S)-ethyl lactate. The key intermediates in the synthesis are two differentially protected hydroxyl aldehydes, i.e. the 4-deoxy-L-threose derivative 3b and the (S,S)-4,5-dihydroxyhexanal derivative 4b which are obtained in high yield starting from O-benzyloxymethyl (S)-ethyl lactate (5). The selective C5 hydroxyl deprotection in 4b leads to the TBS-protected rhodinose 2b in the pyranose form. A complete 1H and 13C NMR analysis of 2b is provided. © 1989.