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The development and application of the asymmetric synthesis of oligosaccharides from achiral starting materials is reviewed. This de novo asymmetric approach centers around the use of asymmetric catalysis for the synthesis of optically pure furan alcohols in conjunction with Achmatowicz oxidative rearrangement for the synthesis of various pyranones. In addition, the use of a diastereoselective palladium-catalyzed glycosylation and subsequent diastereoselective post-glycosylation transformation was used for the synthesis of oligosaccharides. The application of this approach to oligosaccharide synthesis is discussed.
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Synthesis of isobemisiose, neosartose, and fischerose: three α-1,6-linked trehalose-based oligosaccharides identified from Neosartorya fischeri
Three complex α-1,6-linked trehalose-based oligosaccharides with unique preservation properties, isobemisiose, neosartose, and fischerose, were recently identified from the extreme stress-tolerant ascospores of Neosartorya fischeri. Herein, we report the first concise, scalable, and iterative chemical synthesis of these oligosaccharides from a differentially protected thioglycoside donor and a selectively protected, asymmetric trehalose acceptor. This work constitutes an improved synthesis of isobemisiose, and is also the first reported synthesis of neosartose, a tetrasaccharide, and fischerose, a pentasaccharide, in good yield. Importantly, in-depth studies of biological function are enabled by this synthetic platform.
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- Award ID(s):
- 1708546
- PAR ID:
- 10183814
- Date Published:
- Journal Name:
- RSC Advances
- Volume:
- 10
- Issue:
- 38
- ISSN:
- 2046-2069
- Page Range / eLocation ID:
- 22726 to 22729
- Format(s):
- Medium: X
- Sponsoring Org:
- National Science Foundation
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- Free Publicly Accessible Full Text
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Accepted Manuscript1.0
- Journal Article:
- https://doi.org/10.1039/D0RA04137H
