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Glycosylation of methyl-2,3-di-O-acetyl-β-D-xylopyranoside triarylmethyl ethers with electron-donor substituents in the aromatic ring by 3,4-di-O-acetyl-1,2-O-[1-(endo-cyano)-ethylidene]-α-D-xylo-pyranose

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    4-O-(p-Tolyldiphenylmethyl)-, 4-O-(di-p-tolylphenylmethyl) and 4-O-(p-anisyldiphenyl-raethyl) derivatives of methyl-2,3,-di-O-acetyl-β-D-xylopyranoside were synthesized.

  2. 2.

    A study of the reaction of the above compounds with 3,4-di-O-acetyl-1,2-O-[1-(endo-cyano)ethylidene]-α-D-xylopyranose showed that exchange of the trityl group in methyl-2,3-di-O-acetyl-4-O-trityl-β-D-xylopyranoside for triarylmethyl groups containing electron-donor substituents in the aromatic ring does not appreciably affect the stereochemistry of the glycosylation, but can lead to decrease in the yield of the disaccharides.

  3. 3.

    A trans-triarylmethylation reaction was discovered with the reaction of methyl-2,3-di-O-acetyl-4-O-(p-anisyldiphenylmethyl)-β-D-xylopyranoside with triphenylmethylium perchlorate as an example.

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

    N. E. Nifant'ev, L. V. Bakinovskii, Yu. E. Tsvetkov & N. K. Kochetkov

Authors
  1. N. E. Nifant'ev
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  2. L. V. Bakinovskii
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  3. Yu. E. Tsvetkov
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  4. N. K. Kochetkov
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 914–920, April, 1987.

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Nifant'ev, N.E., Bakinovskii, L.V., Tsvetkov, Y.E. et al. Glycosylation of methyl-2,3-di-O-acetyl-β-D-xylopyranoside triarylmethyl ethers with electron-donor substituents in the aromatic ring by 3,4-di-O-acetyl-1,2-O-[1-(endo-cyano)-ethylidene]-α-D-xylo-pyranose. Russ Chem Bull 36, 840–847 (1987). https://doi.org/10.1007/BF00962335

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  • DOI: https://doi.org/10.1007/BF00962335

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