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X-ray and NMR studies on the rotational isomerism about the C(5)-C(6) bond of 6-substituted methyl 2,3,4,-tri-O-acetyl-6-X-α-D-glucopyranoside derivatives

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Abstract

The rotamers about the C(5)–C(6) bond of a series of 2,3,4-tri-O-acetyl-6-X-α-D-glucopyranozide derivatives resulting by substitution at C(6) or O(6) have been studies with1H-NMR spectroscopy (400 MHz) and X-ray structure analysis. The methyl 2,3,4-tri-O-acetyl-6-O-triphenylmethyl-α-D-glucopyranoside and the N-(I-O-methyl-2,3,4-tri-O-acetyl-α-D-glucopyranose-6-yl)-pyridinium nitrate crystallize in the P21 space group with α=14.940(1),b=11.232(1),c=9.0773(7), and β=94.480(7) anda=7.670(1),b=15.384(3),c=9.624(1) and β=104.90(1), respectively; the methyl 2,3,4-tri-O-acetyl-6-O-nitro-α-D-glucopyranoside and methyl 2,3,4-tri-O-acetyl-6-O-deoxy-6-iodo-α-D-glucopyrano-side crystallize in the P212121 space group witha=5.630(1),b=14.360(1) andc=22.388(3), anda=5.556(1),b=14.303(6) andc=21.963(6), respectively.

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Authors and Affiliations

  1. Physics Lab., Agricultural Univ. of Athens, Iera Odos 75, 11855, Athens, Greece

    D. Mentzafos & A. Hountas

  2. Chem. Lab., Agricultural Univ. of Athens, Iera Odos 75, 11855, Athens, Greece

    M. Polissiou, I. Grapsas & M. Georgiadis

  3. N.C.P.S., “Democritos”, Institutute of Material Science, Aghia Paraskevi, 15310, Athens, Greece

    A. Terzis

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  1. D. Mentzafos
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  2. M. Polissiou
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  4. A. Hountas
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  5. M. Georgiadis
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Mentzafos, D., Polissiou, M., Grapsas, I. et al. X-ray and NMR studies on the rotational isomerism about the C(5)-C(6) bond of 6-substituted methyl 2,3,4,-tri-O-acetyl-6-X-α-D-glucopyranoside derivatives. J Chem Crystallogr 25, 157–164 (1995). https://doi.org/10.1007/BF01666100

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  • DOI: https://doi.org/10.1007/BF01666100

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