171006-67-0Relevant academic research and scientific papers
A New Approach to C-Branched Monosaccharides by the Stereoselective Hydrodesulfurization of Methyl 4,6-O-Benzylidene-3--3-deoxy-α-D-erythro-hexopyranosid-2-ulose
Peseke, Klaus,Thiele, Gabriela,Michalik, Manfred
, p. 1633 - 1636 (2007/10/02)
The stereoselective reduction of methyl 4,6-O-benzylidene-3--3-deoxy-α-D-erythro-hexopyranosid-2-ulose 1 with sodium tetrahydridoborate and tributyltin hydride, respectively, to (Z)-configured 4 is described.The increased reactivity of 4 compared to 1 is reflected in several substitution reactions resulting in the displacement of the methylthio group by different N nucleophiles.The substitution products 6-8 were stereoselectively obtained as (Z) isomers.Pyranopyrazole derivatives 3 and 10 were prepared by treatment of 1 and 4, respectively, with hydrazine hydrate. - Keywords: Sugars, branched-chain / α-Oxoketene dithioacetals / Pyranopyrazoles / Hydrodesulfurization, stereoselective / Tributyltin hydride
