Parallel synthesis of multi-branched oligosaccharides related to elicitor active pentasaccharide in rice cell based on orthogonal deprotection and glycosylation strategy

✍ Scribed by Hiroshi Tanaka; Toru Amaya; Takashi Takahashi

• Book ID: 104253372
• Publisher: Elsevier Science
• Year: 2003
• Tongue: French
• Weight: 417 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(03)00553-7

✦ Synopsis

We describe a parallel and efficient synthesis of multi-branched oligosaccharides 3a-g based upon the structure of the phytoalexin elicitor active branched pentasaccharide 2. One-pot sequential orthogonal deprotection of tetrasaccharide 5 with three different protecting groups provided each of seven glycosyl acceptors 4a-g. Glycosylation of the acceptors 4a-g, followed by deprotection provided branched oligosaccharides 3a-g. All the reaction processes from scaffold 5 to 3a-g except for final hydrogenolysis were achieved utilizing an automated synthesizer in a parallel fashion.