ChemInform Abstract: Conversion of p-Methoxyphenyl Glycosides into the Corresponding Glycosyl Chlorides and Bromides, and into Thiophenyl Glycosides.

✍ Scribed by Z. ZHANG; G. MAGNUSSON

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 35 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199717204

✦ Synopsis

Conversion of p-Methoxyphenyl Glycosides into the Corresponding Glycosyl Chlorides and Bromides, and into Thiophenyl Glycosides. -p-Methoxyphenyl glycosides (cf. (III)), which are easily obtained from the corresponding 1-O-acetyl sugars (I), react with acyl halides in the presence of various Lewis acids to furnish the corresponding glycosyl halides (cf. (IV), (V)) in high yield. BF3•OEt2-promoted reaction of p-methoxyphenyl glycosides (III) with thiophenol affords the corresponding thiophenyl glycosides (cf. (VII)) in high yield and excellent β-selectivity. The glycosides (III) prove to be stable under oligosaccharide synthesis conditions.