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A Convenient Approach to the Synthesis of Glycosphingolipids via the Acidic Decyclization of Hexo-O-acetyl-d-gentiobial

Alexander Genrikhovich Tolstikov ¹

Alexander Genrikhovich Tolstikov

Oleg Fedorovich Prokopenko ²

Oleg Fedorovich Prokopenko

Radik Khalyafovich Yamilov ²

Radik Khalyafovich Yamilov

Genrikh Alexandrovich Tolstikov ³

Genrikh Alexandrovich Tolstikov

¹ G.K. Boreskov Institute of Catalysis, Siberian Branch of the Russian Academy of Sciences, Novosibirsk, Russian Federation

² Ufa Institute of Chemistry, Ufa Federal Research Centre of the Russian Academy of Sciences, Ufa, Russian Federation

³ N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk, Russian Federation

10.1070/MC1991v001n02ABEH000038

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Published 1991-06-30

Communication , Volume 1, Issue 2, 64-65

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Tolstikov A. G. et al. A Convenient Approach to the Synthesis of Glycosphingolipids via the Acidic Decyclization of Hexo-O-acetyl-d-gentiobial // Mendeleev Communications. 1991. Vol. 1. No. 2. pp. 64-65.

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Tolstikov A. G., Prokopenko O. F., Yamilov R. K., Tolstikov G. A. A Convenient Approach to the Synthesis of Glycosphingolipids via the Acidic Decyclization of Hexo-O-acetyl-d-gentiobial // Mendeleev Communications. 1991. Vol. 1. No. 2. pp. 64-65.

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TY - JOUR

DO - 10.1070/MC1991v001n02ABEH000038

UR - https://mendcomm.colab.ws/publications/10.1070/MC1991v001n02ABEH000038

TI - A Convenient Approach to the Synthesis of Glycosphingolipids via the Acidic Decyclization of Hexo-O-acetyl-d-gentiobial

T2 - Mendeleev Communications

AU - Tolstikov, Alexander Genrikhovich

AU - Prokopenko, Oleg Fedorovich

AU - Yamilov, Radik Khalyafovich

AU - Tolstikov, Genrikh Alexandrovich

PY - 1991

DA - 1991/06/30

PB - Mendeleev Communications

SP - 64-65

IS - 2

VL - 1

ER -

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@article{1991_Tolstikov,

author = {Alexander Genrikhovich Tolstikov and Oleg Fedorovich Prokopenko and Radik Khalyafovich Yamilov and Genrikh Alexandrovich Tolstikov},

title = {A Convenient Approach to the Synthesis of Glycosphingolipids via the Acidic Decyclization of Hexo-O-acetyl-d-gentiobial},

journal = {Mendeleev Communications},

year = {1991},

volume = {1},

publisher = {Mendeleev Communications},

month = {Jun},

url = {https://mendcomm.colab.ws/publications/10.1070/MC1991v001n02ABEH000038},

number = {2},

pages = {64--65},

doi = {10.1070/MC1991v001n02ABEH000038}

}

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Tolstikov, Alexander Genrikhovich, et al. “A Convenient Approach to the Synthesis of Glycosphingolipids via the Acidic Decyclization of Hexo-O-acetyl-d-gentiobial.” Mendeleev Communications, vol. 1, no. 2, Jun. 1991, pp. 64-65. https://mendcomm.colab.ws/publications/10.1070/MC1991v001n02ABEH000038.

Abstract

The mercury sulphate catalysed acidic opening of the dihydropyran ring in hexa-O-acetyl-D-gentiobial 2, resulting in (2E,4S,5R)-4-acetoxy-5-hydroxy-6-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)hex-2-enal 3 was employed as the key transformation in the synthesis of O-glycosides, which are precursors of glycosphingolipids.

References

10.1055/s-1990-26932

Acidic Opening of the Dihydropyran Ring of Hexa-O-acetyl-D-lactal and Subsequent Chain Elongation. Novel Approach to the Synthesis of Low Molecular WeightO-Glycosides Containing a Diacetoxypolyene Aglycone Moiety

Tolstikov G.A., Tolstikov A.G., Prokopenko O.F., Khalilov L.M., Odinokov V.N.

Synthesis, 1990

10.1039/jr9360001403

304. Optical rotatory dispersion in the carbohydrate group. Part VII. The glucal series

Harris T.L., Herbert R.W., Hirst E.L., Wood C.E., Woodward H.

Journal of the Chemical Society (Resumed), 1936