Hydroxy group interactions in stannylated carbohydrates. Structures and thermal stabilities of 5-deoxy-5-C(Ph3Sn)-1,2-O-isopropylidene-a-D-xylofuranose, 5-deoxy-5-C-(Iph2Sn)-1,2-O-isopropylidene-a-D- and -L-xylofuranose, and 5-deoxy-5-C-(I2PhSn)

L. A. Burnett, V. F. Ferreira, Robert Alan Howie, H. Rufino, Janet Mabel Scott Skakle, J. L. Wardell, S. M. S. V. Wardell

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Abstract

Structures and thermal stabilities of 5-deoxy-5-C-(Ph3Sn)-1,2-O-isopropylidene-alpha-D-xylofuranose, [(D)-3], 5-deoxy-5- C-(IPh2Sn)-1,2-O-isopropylidene-alpha-D- and -L-xylofuranose, [(D)-4 and (L)-4], and 5-deoxy-5-C-(I2PhSn)-1,2-O-isopropylidene- -alpha-D- and -L-xylofuranose, [(D)-5 and (L)-5], are reported. The hydroxy groups in the stannylated xylofuranose derivatives, 3-5, exhibit roles as Lewis bases, Bronsted acids and hydrogen bonding centres. The 5-deoxy- 1,2-O-isopropylidene-alpha-D- and -L-xylofuran-5-yl ligands operate as C-5,O-4 chelating ligands (4-membered chelate rings) in 3, C-5,O-3 chelating ligands in 4 (molecule 2) and 5 (5-membered chelate rings), and a C-5,O-4,O-3 tridentate ligand in 4 (molecule 1) [both 4- and 5-membered chelate rings]. Compounds 4, in contrast to 3 and 5, undergo slow proton-dephenylation reactions in chloroform solutions at ambient temperature. All decompose on heating at 145-155 degreesC with evolution of PhH, Me2CO and H2O. The trigonal bipyramidal tin centres in (D)-5 and (L)-5 are chiral, at least in the solid state. Different modes of O-H-O bonding are found in 3, 4 (molecule 2) and 5 compared to that in 4 (molecule 1).

Original languageEnglish
Pages (from-to)2288-2300
Number of pages12
JournalJournal of the Chemical Society, Perkin Transactions 1
Volume1
DOIs
Publication statusPublished - 2002

Keywords

  • X-RAY-DIFFRACTION
  • MOLECULAR-STRUCTURE
  • MULTINUCLEAR NMR
  • SOLUTION-STATE
  • DERIVATIVES
  • CRYSTAL
  • LIGANDS
  • ESTERS
  • RING

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