A new approach toC-branched monosaccharides by the stereoselective hydrodesulfurization of methyl 4,6-O-benzylidene-3-[bis(methylthio)-methylene]-3-deoxy-α-D-erythro-hexopyranosid-2-ulose

✍ Scribed by Peseke, Klaus ;Thiele, Gabriela ;Michalik, Manfred

• Publisher: John Wiley and Sons
• Year: 1995
• Tongue: English
• Weight: 486 KB
• Volume: 1995
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.1995199509226

✦ Synopsis

Abstract

The stereoselective reduction of methyl 4,6‐O‐benzylidene‐3‐[bis(methylthio)methylene]‐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. Pyrano[3,4‐c]pyrazole derivatives 3 and 10 were prepared by treatment of 1 and 4, respectively, with hydrazine hydrate.