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.

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

DONDONI, Alessandro;FANTIN, Giancarlo;FOGAGNOLO, Marco;PEDRINI, Paola
1989

Abstract

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.
1989
Dondoni, Alessandro; Fantin, Giancarlo; Fogagnolo, Marco; Pedrini, Paola
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11392/462456
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