Structure of α-hydroximinopentyl 1-thio-β-D-glucopyranoside

Tocher, Derek A.; Truter, Mary R.

doi:10.1107/s0108270189013508

Cited by 1 publication

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References 10 publications

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“…hydroximate substituent. The anomeric C-S bond length of 1.803 (3) Å compares with the value of 1.809 Å reported for another -thiohydroximate derivative (Tocher & Truter, 1990), but is significantly shorter than that observed for a similar -thiohydroximate, for which the C-S bond length was reported to be 1.838 Å (Durier et al, 1992), which is consistent with a strong structural anomeric effect expected for this electronegative substituent (Kirby, 1983). The four C-OAc bond lengths in (9) range from 1.436 (3) to 1.444 (3) Å .…”

Section: Figuresupporting

confidence: 74%

Preparation and X-ray analysis of potassium (2,3-dichlorophenyl)glucosinolate

Trenerry²,

Rochfort

et al. 2014

Acta Crystallogr C

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There has been much interest in obtaining crystals for crystallographic analysis of biologically active glucosinolates. Crystals of potassium (2,3-dichlorophenyl)glucosinolate were obtained as a dual solvate, containing one methanol and one ethanol molecule of crystallization, K(+)·C13H14Cl2NO9S2(-)·CH3OH·C2H5OH. The three-dimensional polymeric network consists of chains containing the potassium ions coordinated and bridged by sugar O atoms, which run parallel to the a axis and are further crosslinked through the sugar molecules. The channels of this network are occupied by the dichlorophenyl substituents and the ethanol and methanol solvent molecules. The structure of the S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,3-dichlorophenylacetothiohydroxymate, C21H23Cl2NO10S, precursor has also been determined and the β-configuration and Z isomer of the thiohydroximate substituent is confirmed.

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Section: Figuresupporting

confidence: 74%