Synthesis, regioselective hydrogenolysis, partial hydrogenation, and conformational study of dioxane and dioxolane-type (9′-anthracenyl)methylene acetals of sugars

Zsolt Jakab, Attila Mándi, Anikó Borbás, Attila Bényei, István Komáromi, László Lázár, Sándor Antus, András Lipták

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11 Citations (Scopus)

Abstract

Dioxane-type (9′-anthracenyl)methylene acetal of methyl 2,3-di-O-methyl-α-d-glucopyranoside was cleaved with LiAlH4/AlCl3 (3:1) or with Na(CN)BH3-HCl regioselectively to provide the 4- or 6-O-(9′-anthracenyl)methyl ether, respectively. Hydrogenolytic reaction of the exo and endo isomers of dioxolane-type acetals proved to be directed by the configuration of the acetalic carbon as well as by the intramolecular participation of the adjacent-free hydroxyl; ring-opening reaction of the endo isomer of the methyl 2,3-O-(9′-anthracenyl)methylene-α-l-rhamnopyranoside took place with complete selectivity resulting in the axial (9′-anthracenyl)methyl ether, whereas a 1:1 mixture of the axial and equatorial ethers was formed upon the same reaction of the exo isomer. Catalytic hydrogenation of the sugar acetals resulted in (9′,10′-dihydro-9′-anthracenyl)methylene derivatives without affecting the acetalic center. High-temperature molecular dynamics simulations and DFT (Density Functional Theory) geometry optimizations were carried out to study the conformation of the dioxane-type (9′,10′-dihydro-9′-anthracenyl)methylene acetal.

Original languageEnglish
Pages (from-to)2444-2453
Number of pages10
JournalCarbohydrate Research
Volume344
Issue number18
DOIs
Publication statusPublished - dec. 14 2009

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ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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