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Simple Stereocontrolled Synthesis of Methyl 2-Deoxy- d - erythro -hexopyranosid-4-uloses, Thromboxane B 2 (TXB 2 ) Precursors, from d -Galactose

1995; Taylor & Francis; Volume: 14; Issue: 4-5 Linguagem: Inglês

10.1080/07328309508005355

1532-2327

Oscar Moradei, Cecile du Mortier, Alicia Fernández Cirelli, Joachim Thiem,

Diet, Metabolism, and Disease

Abstract The stereospecific synthesis of methyl 3-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-α-d-erythro-hexopyranosid-4-ulose (5) - a Thromboxane B2 (TXB2) precursor -starting from D-galactose is described. Facile and established methods including selective benzoylation, oxidation-elimination and a stereocontrolled hydrogenation (Pd/charcoal) were employed effectively.