Development of an intramolecular glycosylation using glycosyl donor having aldehyde group as leaving group

2015 Fiscal Year Final Research Report

• Project/Area Number: 25870140
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Bio-related chemistry; Bioorganic chemistry
• Research Institution: Chiba University
• Principal Investigator: Dohi Hirofumi 千葉大学, 融合科学研究科(研究院), 助教 (10345928)
• Project Period (FY): 2013-04-01 – 2016-03-31
• Keywords: グリコシル化 / 立体選択性 / 位置選択性 / 糖鎖合成 / 反応性 / 脱離基 / アセタール / 化学選択性

Outline of Final Research Achievements

Toward stereoselective construction of 1,2-cis glycosides, we attempted to develop an efficient intramolecular glycosylation methodology using glycosyl donors having thiosalicyl aldehyde as leaving group. Glycosyl donor and acceptor could be tethered regioselectively by acetal linkage using aldehyde group in glycosyl donor, and the conjugate was subjected to glycosylation reaction to confirm if the glycosylation was proceeded intramolecularly or not. When MeOTf was employed as a promoter, conjugates having secondary alcohol showed intramolecular glycosylation whereas those having primary alcohol preferred intermolecular reaction. Alternatively, we found that glycosyl donor having thiosalicyl aldehyde as an aglycon could be chemoselectively activated by TMSOTf alone that is inactive against general thioglycosides.

Free Research Field

複合化学