том 73 издание 13 страницы 1740-1744

Sugar migration induced by the Wagner-Meerwein rearrangement of 28- O -glycosyl-betulin derivatives

Тип публикацииJournal Article
Дата публикации2017-03-01
scimago Q3
wos Q2
БС2
SJR0.426
CiteScore4.1
Impact factor2.2
ISSN00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Краткое описание
Treatment of betulin-type saponins, in which the sugar moiety is connected at the 28-position, with TMSOTf affords 3-O-substituted allobetulin saponins. This unprecedented migration of the sugar part is driven by the Wagner-Meerwein rearrangement of the betulin core. According to our mechanistic studies an oxocarbenium ion released during the rearrangement reacts with the free 3-OH group of the triterpene affording the final allobetulin saponin. Migration rate depends on the size and configuration of the sugar moiety.
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ГОСТ |
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Korda A. et al. Sugar migration induced by the Wagner-Meerwein rearrangement of 28- O -glycosyl-betulin derivatives // Tetrahedron. 2017. Vol. 73. No. 13. pp. 1740-1744.
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Korda A., Pakulski Z., Cmoch P., Gwardiak K., Karczewski R. Sugar migration induced by the Wagner-Meerwein rearrangement of 28- O -glycosyl-betulin derivatives // Tetrahedron. 2017. Vol. 73. No. 13. pp. 1740-1744.
RIS |
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TY - JOUR
DO - 10.1016/j.tet.2017.02.024
UR - https://doi.org/10.1016/j.tet.2017.02.024
TI - Sugar migration induced by the Wagner-Meerwein rearrangement of 28- O -glycosyl-betulin derivatives
T2 - Tetrahedron
AU - Korda, Anna
AU - Pakulski, Zbigniew
AU - Cmoch, Piotr
AU - Gwardiak, Katarzyna
AU - Karczewski, Romuald
PY - 2017
DA - 2017/03/01
PB - Elsevier
SP - 1740-1744
IS - 13
VL - 73
SN - 0040-4020
SN - 1464-5416
ER -
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@article{2017_Korda,
author = {Anna Korda and Zbigniew Pakulski and Piotr Cmoch and Katarzyna Gwardiak and Romuald Karczewski},
title = {Sugar migration induced by the Wagner-Meerwein rearrangement of 28- O -glycosyl-betulin derivatives},
journal = {Tetrahedron},
year = {2017},
volume = {73},
publisher = {Elsevier},
month = {mar},
url = {https://doi.org/10.1016/j.tet.2017.02.024},
number = {13},
pages = {1740--1744},
doi = {10.1016/j.tet.2017.02.024}
}
MLA
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Korda, Anna, et al. “Sugar migration induced by the Wagner-Meerwein rearrangement of 28- O -glycosyl-betulin derivatives.” Tetrahedron, vol. 73, no. 13, Mar. 2017, pp. 1740-1744. https://doi.org/10.1016/j.tet.2017.02.024.