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. 2010 Apr 12;49(17):3049-52.
doi: 10.1002/anie.200907178.

Stereoselective synthesis of alpha-keto-deoxy-D-glycero-D-galacto-nonulosonic acid glycosides by means of the 4,5-O-carbonate protecting group

David Crich  1 , Chandrasekhar Navuluri
Affiliations

Stereoselective synthesis of alpha-keto-deoxy-D-glycero-D-galacto-nonulosonic acid glycosides by means of the 4,5-O-carbonate protecting group

David Crich et al. Angew Chem Int Ed Engl. .

Abstract

A 1-adamantyl thioglycoside derivative of KDN, derived from N-acetylneuraminic acid, carrying a 3,4-O-carbonate protecting group is a highy efficient and α-selective KDN donor on activation with NIS and TfOH in dichloromethane and acetonitrile at −78 °C. Glycosylations conducted with this protecting group do not suffer from competing glycal formation. Seven examples are given, including the use of galactose 3- and 6-hydroxy groups.

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Figures

Figure 1
Figure 1
Hypothetical Intermediate Stabilized by the Presence of the Cyclic Carbonate
Scheme 1
Scheme 1
Donor synthesis. Ada = 1-adamantanyl, pTSA = para-toluenesulfonic acid.
Scheme 2
Scheme 2
Synthesis of an authentic sample of glycal. mCPBA = meta-chloroperoxybenzoic acid.
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References

    1. Varki A. Glycobiol. 1993;3:97–130. - PMC - PubMed
    2. Schauer R. Adv. Carbohydr. Chem. Biochem. 1982;40:131–234. - PubMed
    1. Inoue S, Kitajima J. Glycoconj. J. 2006;23:277–290. - PubMed
    2. Inoue S, Poongodi GL, Suresh N, Chang T, Inoue Y. Glycoconj. J. 2006;23:401–410. - PubMed
    1. Kajihara Y, Akai S, Nakagawa T, Sato R, Ebata T, Kodama H, Sato K-i. Carbohydr. Res. 1999;315:137–141. - PubMed
    2. Blixt O, Paulson JC. Adv. Synth. Catal. 2006;345:687–690.
    1. Chen C-C, Ress D, Linhardt RJ. ACS Symposium Series. 2005;896:53–80.
    2. Boons G-J, Demchenko AV. In: Carbohydrate-Based Drug Discovery. Wong C-H, editor. Vol. 1. Weinheim: WILEY-VCH; 2003. pp. 55–102.
    3. Kiso M, Ishida H, Ito H. In: Carbohydrates in Chemistry and Biology. Ernst B, Hart GW, Sinaÿ P, editors. Vol. 1. Weinheim: WILEY-VCH; 2000. pp. 345–365.
    4. Ando H. Trends Glycosci. Glycotech. 2008;20:141–158.
    1. Tanaka H, Nishiura Y, Takahashi T. J. Am. Chem. Soc. 2006;128:7124–7125. - PubMed
    2. Tanaka H, Nishiura Y, Takahashi T. J. Org. Chem. 2009;74:4383–4386. - PubMed

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