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N- and C-Glycosylation of 6,7-Difluoro-1,4-dihydro-4-oxo-3-quinoline Carboxylic Acid Ethyl Ester

Genrikh Alexandrovich Tolstikov 1
Genrikh Alexandrovich Tolstikov
, 
Akhat Gaziz'yanovich Mustafin 2
Akhat Gaziz'yanovich Mustafin
, 
Guzel Kh Yghibaeva 2
Guzel Kh Yghibaeva
, 
Rail Rafkatovich Gataullin 2
Rail Rafkatovich Gataullin
, 
Leonid Vasilevich Spirikhin 2
Leonid Vasilevich Spirikhin
, 
Venera Serazetdinovna Sultanova 2
Venera Serazetdinovna Sultanova
, 
Ildus Barievich Abdrakhmanov 2
Ildus Barievich Abdrakhmanov
10.1070/MC1993v003n05ABEH000284
Published 1993-10-30
Communication , Volume 3, Issue 5, 194-194
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Tolstikov G. A. et al. N- and C-Glycosylation of 6,7-Difluoro-1,4-dihydro-4-oxo-3-quinoline Carboxylic Acid Ethyl Ester // Mendeleev Communications. 1993. Vol. 3. No. 5. pp. 194-194.
GOST all authors (up to 50) Copy
Tolstikov G. A., Mustafin A. G., Yghibaeva G. Kh., Gataullin R. R., Spirikhin L. V., Sultanova V. S., Abdrakhmanov I. B. N- and C-Glycosylation of 6,7-Difluoro-1,4-dihydro-4-oxo-3-quinoline Carboxylic Acid Ethyl Ester // Mendeleev Communications. 1993. Vol. 3. No. 5. pp. 194-194.
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TY - JOUR
DO - 10.1070/MC1993v003n05ABEH000284
UR - https://mendcomm.colab.ws/publications/10.1070/MC1993v003n05ABEH000284
TI - N- and C-Glycosylation of 6,7-Difluoro-1,4-dihydro-4-oxo-3-quinoline Carboxylic Acid Ethyl Ester
T2 - Mendeleev Communications
AU - Tolstikov, Genrikh Alexandrovich
AU - Mustafin, Akhat Gaziz'yanovich
AU - Yghibaeva, Guzel Kh
AU - Gataullin, Rail Rafkatovich
AU - Spirikhin, Leonid Vasilevich
AU - Sultanova, Venera Serazetdinovna
AU - Abdrakhmanov, Ildus Barievich
PY - 1993
DA - 1993/10/30
PB - Mendeleev Communications
SP - 194-194
IS - 5
VL - 3
ER -
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@article{1993_Tolstikov,
author = {Genrikh Alexandrovich Tolstikov and Akhat Gaziz'yanovich Mustafin and Guzel Kh Yghibaeva and Rail Rafkatovich Gataullin and Leonid Vasilevich Spirikhin and Venera Serazetdinovna Sultanova and Ildus Barievich Abdrakhmanov},
title = {N- and C-Glycosylation of 6,7-Difluoro-1,4-dihydro-4-oxo-3-quinoline Carboxylic Acid Ethyl Ester},
journal = {Mendeleev Communications},
year = {1993},
volume = {3},
publisher = {Mendeleev Communications},
month = {Oct},
url = {https://mendcomm.colab.ws/publications/10.1070/MC1993v003n05ABEH000284},
number = {5},
pages = {194--194},
doi = {10.1070/MC1993v003n05ABEH000284}
}
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Tolstikov, Genrikh Alexandrovich, et al. “N- and C-Glycosylation of 6,7-Difluoro-1,4-dihydro-4-oxo-3-quinoline Carboxylic Acid Ethyl Ester.” Mendeleev Communications, vol. 3, no. 5, Oct. 1993, pp. 194-194. https://mendcomm.colab.ws/publications/10.1070/MC1993v003n05ABEH000284.

Abstract

1,2,3,4,6-Penta-O-acetyl-α-D-glucopyranose reacts with a silylated ethyl ester of 6,7-difluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid 1 with C-glycosylation to subsequently afford the ethyl ester of 8-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)- 6,7-difluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid 4; on the contrary, condensation of 1,2-di-O-acetyl-3,5-di-O-benzoyl- D-xylofuranose with the heterocycle 1 results in an N-glycosylation product 2.

References

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Khim.-Pharm. Zh., 1989
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G.A. Tolstikov, A.G. Mustafin, R.R. Gataullin, V.S. Sultanova, L.V. Spirikhin and I.B. Abdrakhmanov. Izv Akad.Nauk, Ser. Khim., in press.
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Bioorg. Khim., 1976