Janus glycosides of next generation

Synthesis of 4-(3-chloropropoxy)phenyl and 4-(3-azidopropoxy)phenyl glycosides

Elena V. Stepanova, Polina I. Abronina, Alexander I. Zinin, Alexander O. Chizhov, Leonid O. Kononov

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Efficient procedures for the preparative synthesis of per-O-acyl derivatives of 4-(3-chloropropoxy)phenyl (CPP) glycosides of a series of common mono- and disaccharides (D-glucose, D-galactose, D-mannose, L-rhamnose, D-arabinofuranose, D-glucosamine, lactose) are described. The CPP glycosides obtained were transformed in almost quantitative yields to the corresponding unprotected 4-(3-azidopropoxy)phenyl (APP) glycosides, which could become next-generation Janus glycosides with cleavable spacer aglycon, ready for conjugation or further transformation.

Original languageEnglish
Pages (from-to)95-104
Number of pages10
JournalCarbohydrate Research
DOIs
Publication statusPublished - 1 Jan 2019

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Glycosides
Rhamnose
Monosaccharides
Disaccharides
Glucosamine
Lactose
Mannose
Galactose
Derivatives
Glucose

Keywords

  • Cleavable aglycon
  • Glycosylation
  • Janus aglycon
  • Spacer aglycon

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

Cite this

Janus glycosides of next generation : Synthesis of 4-(3-chloropropoxy)phenyl and 4-(3-azidopropoxy)phenyl glycosides. / Stepanova, Elena V.; Abronina, Polina I.; Zinin, Alexander I.; Chizhov, Alexander O.; Kononov, Leonid O.

In: Carbohydrate Research, 01.01.2019, p. 95-104.

Research output: Contribution to journalArticle

Stepanova, Elena V. ; Abronina, Polina I. ; Zinin, Alexander I. ; Chizhov, Alexander O. ; Kononov, Leonid O. / Janus glycosides of next generation : Synthesis of 4-(3-chloropropoxy)phenyl and 4-(3-azidopropoxy)phenyl glycosides. In: Carbohydrate Research. 2019 ; pp. 95-104.
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