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2-Nitroglycals : versatile intermediates for efficient and highly stereoselective base-catalyzed glycoside bond formations

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2008

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Reddy, B. Gopal

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https://doi.org/10.1038/nprot.2007.495
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Nature Protocols. Nature Publishing Group. 2008, 3(1), pp. 114-121. ISSN 1754-2189. eISSN 1750-2799. Available under: doi: 10.1038/nprot.2007.495

Zusammenfassung

This protocol describes the O-glycosyl trichloroacetimidate-based glycosylation of protected galactal 1 as acceptor under Sn(OTf)2 catalysis to give disaccharide 4. Nitration of the galactal moiety using nitric acid–acetic acid as nitrating agent followed by base-promoted acetic acid elimination affords the 2-nitro derivative 6 in a one-pot procedure. These types of intermediates can be used in the stereoselective synthesis of glycosides via Michael-type addition of alcohols as nucleophiles to 2-nitroglycals. Here, the base-catalyzed α-selective addition of N-Boc-protected Ser and Thr esters (7a, b) is described, which leads stereoselectively to adducts 8a, b. Transformation into the corresponding 2a-acetylamino derivates 9a, b provides versatile mucin core 1 building blocks (the total time for synthesizing 9a, b starting from 1 to 2 is typically 7 d with an overall yield of 18–25%). Also various other types of nucleophiles are amenable to this Michael-type addition 2-nitroglycals.

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540 Chemie

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ISO 690REDDY, B. Gopal, Richard R. SCHMIDT, 2008. 2-Nitroglycals : versatile intermediates for efficient and highly stereoselective base-catalyzed glycoside bond formations. In: Nature Protocols. Nature Publishing Group. 2008, 3(1), pp. 114-121. ISSN 1754-2189. eISSN 1750-2799. Available under: doi: 10.1038/nprot.2007.495
BibTex
@article{Reddy20082Nitr-58588,
  year={2008},
  doi={10.1038/nprot.2007.495},
  title={2-Nitroglycals : versatile intermediates for efficient and highly stereoselective base-catalyzed glycoside bond formations},
  number={1},
  volume={3},
  issn={1754-2189},
  journal={Nature Protocols},
  pages={114--121},
  author={Reddy, B. Gopal and Schmidt, Richard R.}
}
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