One-pot synthesis of cyclic oligosaccharides by the polyglycosylation of monothioglycosides

Hidehisa Someya, Takehito Seki, Gota Ishigami, Taiki Itoh, Yutaka Saga, Yasuyuki Yamada, Shin Aoki

Research output: Contribution to journalArticle

Abstract

Cyclic oligosaccharides such as cyclodextrins (CyDs) have been known as excellent host molecules for the inclusion of various organic guest molecules. The development of new synthetic methods for preparing cyclic oligosaccharides from simple and readily available glycosyl donors would be highly desirable, since the current traditional synthetic routes include multiple reaction steps (glycosylation reactions and deprotections). We herein report on the synthesis of cyclic oligosaccharides by polyglycosylation of monothioglycosides, typically, 2,3,4-protected 1-thioglycosides. A series of promoters and solvents were tested for the glycosylation of thiogalactosides that contain a hydroxy group at the 6-position, and glycosylation using a N-iodosuccinimide (NIS)/trimethylsilyl triflate (TMSOTf) promoter system in dichloromethane afforded cyclic oligosaccharides which consist of tri~penta galactosides containing repeating β-(1→6) glycosidic linkage as major products, as evidenced by a single crystal X-ray structure analysis of the cyclic tetragalactoside. The effect of reaction temperature and reactant concentrations on the glycosylation products was also investigated. The cyclic glucosides were obtained by the glycosylation of the thioglucosides. Moreover, protecting groups of the synthesized cyclic tetragalactoside were removed to obtain deprotected cyclic tetragalactoside.

Original languageEnglish
Article number107888
JournalCarbohydrate Research
Volume487
DOIs
Publication statusPublished - Jan 2020

Fingerprint

Glycosylation
Oligosaccharides
Thioglucosides
Thioglycosides
Thiogalactosides
Galactosides
Rubiaceae
Molecules
Methylene Chloride
Glucosides
Cyclodextrins
Fourier Analysis
X-Rays
Single crystals
X rays
Temperature

Keywords

  • Cyclic oligosaccharide
  • Glycosylation
  • Thiogalactoside
  • Thioglucoside
  • β-(1→6) glycosidic linkage

Cite this

Someya, Hidehisa ; Seki, Takehito ; Ishigami, Gota ; Itoh, Taiki ; Saga, Yutaka ; Yamada, Yasuyuki ; Aoki, Shin. / One-pot synthesis of cyclic oligosaccharides by the polyglycosylation of monothioglycosides. In: Carbohydrate Research. 2020 ; Vol. 487.
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One-pot synthesis of cyclic oligosaccharides by the polyglycosylation of monothioglycosides. / Someya, Hidehisa; Seki, Takehito; Ishigami, Gota; Itoh, Taiki; Saga, Yutaka; Yamada, Yasuyuki; Aoki, Shin.

In: Carbohydrate Research, Vol. 487, 107888, 01.2020.

Research output: Contribution to journalArticle

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AU - Someya, Hidehisa

AU - Seki, Takehito

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