Email this article Are N-phthaloyl and O-allyl protective groups orthogonal?
- Authors: Orlova A.V.1, Volodin D.A.1, Zinin A.I.1, Kononov L.O.1,2
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Affiliations:
- N. D. Zelinskiy Institute of Organic Chemistry, Russian Academy of Sciences
- Moscow Physico-Technical Institute (National Research University)
- Issue: Vol 68, No 9 (2019)
- Pages: 1791-1794
- Section: Brief Communications
- URL: https://journals.rcsi.science/1066-5285/article/view/243487
- DOI: https://doi.org/10.1007/s11172-019-2626-9
- ID: 243487
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Abstract
Using allyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-d-glucopyranoside as a model substrate, it was shown that the degree of orthogonality of N-phthaloyl and O-allyl protective groups under the conditions of hydrazinolysis of the phthalimide group depends on the amount of atmospheric oxygen in the reaction mixture during the reaction and during the work-up procedure.
About the authors
A. V. Orlova
N. D. Zelinskiy Institute of Organic Chemistry, Russian Academy of Sciences
Email: kononov@ioc.ac.ru
Russian Federation, 47 Leninskiy prosp., Moscow, 119991
D. A. Volodin
N. D. Zelinskiy Institute of Organic Chemistry, Russian Academy of Sciences
Email: kononov@ioc.ac.ru
Russian Federation, 47 Leninskiy prosp., Moscow, 119991
A. I. Zinin
N. D. Zelinskiy Institute of Organic Chemistry, Russian Academy of Sciences
Email: kononov@ioc.ac.ru
Russian Federation, 47 Leninskiy prosp., Moscow, 119991
L. O. Kononov
N. D. Zelinskiy Institute of Organic Chemistry, Russian Academy of Sciences; Moscow Physico-Technical Institute (National Research University)
Author for correspondence.
Email: kononov@ioc.ac.ru
Russian Federation, 47 Leninskiy prosp., Moscow, 119991; 9 Institutskiy per., Dolgoprudnyi, Moscow Region, 141701
