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. 2008 Jun 5;10(11):2107-10.
doi: 10.1021/ol800648d. Epub 2008 May 1.

Application of the superarmed glycosyl donor to chemoselective oligosaccharide synthesis

Laurel K Mydock  1 , Alexei V Demchenko
Affiliations

Application of the superarmed glycosyl donor to chemoselective oligosaccharide synthesis

Laurel K Mydock et al. Org Lett. .

Abstract

Recently, we discovered a novel method for "superarming" glycosyl donors. Herein, this concept has been exemplified in one-pot oligosaccharide syntheses, whereby the superarmed glycosyl donor was chemoselectively activated over traditional "armed" and disarmed glycosyl acceptors. Direct side-by-side comparison of the reactivities of the classic armed and superarmed glycosyl donors further validates the credibility of the novel concept.

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Figures

Figure 1
Figure 1
Superarmed glycosyl donors.
Scheme 1
Scheme 1
Chemoselective Sequential Synthesis of Trisaccharides 17 and 18
Scheme 2
Scheme 2
Competitive Glycosidations of Glycosyl Donors 1 and 4 with Glycosyl Acceptor 16 in the Presence of DMTST
See this image and copyright information in PMC

References

    1. Prescher JA, Bertozzi CR. Nat Chem Biol. 2005;1:13–21. - PubMed
    2. Galonic DP, Gin DY. Nature. 2007;446:1000–1007. - PMC - PubMed
    3. Seeberger PH, Werz DB. Nature. 2007;446:1046–1051. - PubMed
    1. Demchenko AV. Advances in Stereoselectivity and Therapeutic Relevance. Wiley-VCH; New York: 2008. Handbook of Chemical Glycosylation.
    1. Boons GJ. Tetrahedron. 1996;52:1095–1121.
    2. Demchenko AV. Lett Org Chem. 2005;2:580–589.
    3. Codee JDC, Litjens REJN, van den Bos LJ, Overkleeft HS, van der Marel GA. Chem Soc Rev. 2005;34:769–782. - PubMed
    1. Mydock LK, Demchenko AV. Org Lett. 2008;10:2103–2106. - PMC - PubMed
    1. Kamat MN, Demchenko AV. Org Lett. 2005;7:3215–3218. - PubMed

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