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New approaches to analogs of α-linked galactosylceramides based on functionalized serinol

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Abstract

New derivatives of serinol, 3-[4-(2-chloroethoxy)benzyloxy]-2-phthalimidopropan-1-ol and 3-[4-(2-azidoethoxy)phenoxy]-2-phthalimidopropan-1-ol, were synthesized and tested as glycosyl acceptors in stereoselective 1,2-cis-galactosylation in the benzyl-free synthesis of analogs of α-linked galactosylceramides. It was found that NIS/AgOTf-promoted glycosylation of 3-[4-(2-chloroethoxy)benzyloxy]-2-phthalimidopropan-1-ol with ethyl 4,6-O-(di-tert-butylsilylene)-1-thio-β-D-galactoside resulted in both the expected α-linked diastereomeric glycosides and the product of iodination of the benzyl group of the aglycon. This process was avoided by using the corresponding galactosyl imidate under Et3SiOTf promotion to give exclusively α-linked diastereometic serinol glycosides.

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Authors and Affiliations

  1. Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3A, 18059, Rostock, Germany

    U. Jost, D. Michalik & U. Kragl

  2. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    P. I. Abronina, A. I. Zinin, N. N. Kondakov, A. O. Chizov, V. I. Torgov & L. O. Kononov

  3. Leibniz Institute for Catalysis (LIKAT), Albert-Einstein-Str. 29a, 18059, Rostock, Germany

    D. Michalik

Authors
  1. U. Jost
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  2. P. I. Abronina
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  3. A. I. Zinin
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  4. D. Michalik
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  5. U. Kragl
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  6. N. N. Kondakov
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  7. A. O. Chizov
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  8. V. I. Torgov
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  9. L. O. Kononov
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Corresponding authors

Correspondence to D. Michalik or N. N. Kondakov.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2297–2306, December, 2018.

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Jost, U., Abronina, P.I., Zinin, A.I. et al. New approaches to analogs of α-linked galactosylceramides based on functionalized serinol. Russ Chem Bull 67, 2297–2306 (2018). https://doi.org/10.1007/s11172-018-2373-3

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  • DOI: https://doi.org/10.1007/s11172-018-2373-3

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