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

Research output: Contribution to journalArticle

1 Citation (Scopus)

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

Cite this

@article{bb103edeac004166a77872aa5a7f7e1c,
title = "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)",
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).",
keywords = "X-RAY-DIFFRACTION, MOLECULAR-STRUCTURE, MULTINUCLEAR NMR, SOLUTION-STATE, DERIVATIVES, CRYSTAL, LIGANDS, ESTERS, RING",
author = "Burnett, {L. A.} and Ferreira, {V. F.} and Howie, {Robert Alan} and H. Rufino and Skakle, {Janet Mabel Scott} and Wardell, {J. L.} and Wardell, {S. M. S. V.}",
year = "2002",
doi = "10.1039/b204675j",
language = "English",
volume = "1",
pages = "2288--2300",
journal = "Journal of the Chemical Society, Perkin Transactions 1",
issn = "1472-7781",
publisher = "Chemical Society",

}

TY - JOUR

T1 - 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)

AU - Burnett, L. A.

AU - Ferreira, V. F.

AU - Howie, Robert Alan

AU - Rufino, H.

AU - Skakle, Janet Mabel Scott

AU - Wardell, J. L.

AU - Wardell, S. M. S. V.

PY - 2002

Y1 - 2002

N2 - 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).

AB - 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).

KW - X-RAY-DIFFRACTION

KW - MOLECULAR-STRUCTURE

KW - MULTINUCLEAR NMR

KW - SOLUTION-STATE

KW - DERIVATIVES

KW - CRYSTAL

KW - LIGANDS

KW - ESTERS

KW - RING

U2 - 10.1039/b204675j

DO - 10.1039/b204675j

M3 - Article

VL - 1

SP - 2288

EP - 2300

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

SN - 1472-7781

ER -