Rapid assembly of branched mannose oligosaccharides through consecutive regioselective glycosylation: A convergent and efficient strategy. Issue 27 (6th July 2017)

• Record Type: Journal Article
• Authors: Meng, Bo; Wang, Jun; Wang, Qianli; Serianni, Anthony S.; Pan, Qingfeng
• Is Part Of: Tetrahedron. Volume 73:Issue 27/28(2017)
• Page Start: 3932
• Page End: 3938
• Publication Date: 2017-07-06
• Subjects: Regioselective glycosylation -- Mannose oligosaccharide -- Glycan; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2017.05.073
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A convergent and efficient strategy for the synthesis of high-mannose oligosaccharides is described wherein regioselective glycosylations between trichloroacetimidate donors and partially protected acceptors are employed to reduce the number of protection–deprotection steps. Two representative branched mannose oligosaccharides, a mannose heptasaccharide (Man7 ) and a mannose nonasaccharide (Man9 ) were constructed via (4 + 3) and (5 + 4) glycosylations, respectively. These mannose-containing oligosaccharides were obtained in nine steps in ∼25% overall yield and >98% purity on 60–70 mg scales to demonstrate the effectiveness of the strategy. Graphical abstract: