Synthesis of sulfur containing macrocycles with sucrose scaffold

Agnieszka Gajewska; Anna Osuch-Kwiatkowska; Sławomir Jarosz

doi:10.1016/j.carres.2019.107825

Synthesis of sulfur containing macrocycles with sucrose scaffold

Carbohydr Res. 2019 Dec 1:486:107825. doi: 10.1016/j.carres.2019.107825. Epub 2019 Sep 26.

Authors

Agnieszka Gajewska¹, Anna Osuch-Kwiatkowska¹, Sławomir Jarosz²

Affiliations

¹ Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224, Warsaw, Poland.
² Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224, Warsaw, Poland. Electronic address: slawomir.jarosz@icho.edu.pl.

PMID: 31580967
DOI: 10.1016/j.carres.2019.107825

Abstract

The first synthesis of sucrose-based macrocycles containing two sulfur atoms in the ring was presented. The synthesis was initiated from known 6,6'-dideoxy-6,6'-di-chloro-1',2,3,3',4,4'-hexa-O-benzyl-sucrose in which both terminal positions (C6 and C6') were elongated by the -S-CH₂-CH₂-OH unit. The resulting diol was converted into dichloride and reacted further with a series of diamines which afforded the corresponding macrocyclic derivatives in high yields.

Keywords: Cyclization; Sucrose; Sulfur macrocycles.

MeSH terms

Chemistry Techniques, Synthetic
Macrocyclic Compounds / chemical synthesis*
Macrocyclic Compounds / chemistry*
Sucrose / chemistry*
Sulfur / chemistry*

Substances

Macrocyclic Compounds
Sucrose
Sulfur