Stereoselective syntheses of acetylated o-tolyl 1-thioglycosides

✍ Scribed by Yili Ding; Yuting Liu

• Publisher: Elsevier Science
• Year: 1991
• Tongue: English
• Weight: 248 KB
• Volume: 209
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(91)80168-m

✦ Synopsis

Many I-thioglycosides and their derivatives are biologically active and some can inhibit the growth and metabolism of cancer cells'. Hence, there has been much interest in the synthesis and properties of these compounds'.

There are several methods for the synthesis of 1-thio-/3-D-glycosides'. Apparu et a1.4 synthesised 1-thio-a-D-glucopyranosides and 1-thio-a-o-galactopyranosides from the corresponding /3-D-glycopyranosyl chlorides in hexamethylphosphoric triamide followed by column chromatography. We now report on the synthesis of the acetylated o-tolyl 1 -thio-D-glycosides l-7 by the condensation of o-toluenethiol with the acetylated a-D-glycosyl bromide or p-D-glycosyl chloride according to the procedure of Purves';