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Russian Chemical Bulletin

, Volume 67, Issue 12, pp 2297–2306 | Cite as

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

  • U. Jost
  • P. I. Abronina
  • A. I. Zinin
  • D. MichalikEmail author
  • U. Kragl
  • N. N. KondakovEmail author
  • A. O. Chizov
  • V. I. Torgov
  • L. O. Kononov
Full Articles
  • 8 Downloads

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.

Key words

1,2-cis-galactosylation serinol galactosylceramide 

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • U. Jost
    • 1
  • P. I. Abronina
    • 2
  • A. I. Zinin
    • 2
  • D. Michalik
    • 1
    • 3
    Email author
  • U. Kragl
    • 1
  • N. N. Kondakov
    • 2
    Email author
  • A. O. Chizov
    • 2
  • V. I. Torgov
    • 2
  • L. O. Kononov
    • 2
  1. 1.Institut für ChemieUniversität RostockRostockGermany
  2. 2.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation
  3. 3.Leibniz Institute for Catalysis (LIKAT)RostockGermany

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