SULFATION OF BETULIN 3-PROPIONATE WITH SULFAMIC ACID IN N,N-DIMETHYLFORMAMIDE MEDIUM

UDC 54.057:543.42

  • Vladimir Aleksandrovich Levdansky Institute of Chemistry and Chemical Technology SB RAS, FRC KSC SB RAS https://orcid.org/0000-0002-6140-2420 Email: vlevdanskij@mail.ru
  • Svetlana Andreevna Novikova Institute of Chemistry and Chemical Technology SB RAS, FRC KSC SB RAS Email: snovik.chem@gmail.com
  • Aleksandr Vladimirovich Levdanskiy Institute of Chemistry and Chemical Technology SB RAS, FRC KSC SB RAS Email: alexsander.l@mail.ru
DOI_disc_logo https://doi.org/10.14258/jcprm.20240315219
Keywords: betulin 3-propionate, sulfation, sulfamic acid, urea, 28-sulfate of betulin 3-propionate

Abstract

A new efficient method for the sulfation of betulin 3-propionate using sulfamic acid –urea mixture in N,N-dimethylformamide medium was developed. This method of synthesis allows to exclude the use of such aggressive sulfating reagents as sulfur dioxide, chlorosulfonic and sulfuric acid. As a result, 28-sulfates of betulin 3-propionate were obtained as ammonium salt, acidic form, potassium salt and sodium salt in 91, 89, 89, 90% yields, respectively. The composition of the obtained samples of 28-sulfate 3-propionate betulin was confirmed by elemental analysis, the sulfur content ranged from 5.03 to 5.32%. The structure of the initial and sulfated betulin 3-propionate was studied by FTIR and 13C NMR spectroscopy. The introduction of sulfate groups into the molecule of betulin 3-propionate was confirmed by the appearance of new absorption bands in the FTIR spectra at 830–833 cm-1 and at 1225–1227 cm-1, which corresponds to the stretching vibrations υ(C–O–S) and to the asymmetric stretching vibrations υas(O=S=O), respectively. It was shown by 13C NMR method that the initial betulin 3-propionate has a C28 carbon atom signal at a chemical shift of 60.6 ppm, while the synthesized as the sodium salt of betulin 3-propionate 28-sulfate has a C28 carbon atom signal at a chemical shift of 66.0 ppm. This indicates a complete substitution of the hydroxyl group of betulin 3-propionate for the sulfate group.

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Author Biographies

Vladimir Aleksandrovich Levdansky, Institute of Chemistry and Chemical Technology SB RAS, FRC KSC SB RAS

Doctor of Chemical Sciences, Leading Researcher of the Laboratory of Chemistry of Natural Organic Raw Materials

Svetlana Andreevna Novikova, Institute of Chemistry and Chemical Technology SB RAS, FRC KSC SB RAS

Candidate of Chemical Sciences, Researcher of the Laboratory of Molecular Spectroscopy and Analysis

Aleksandr Vladimirovich Levdanskiy , Institute of Chemistry and Chemical Technology SB RAS, FRC KSC SB RAS

Candidate of Chemical Sciences, Researcher of the Laboratory of Chemistry of Natural Organic Raw Materials

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Published
2024-09-26
How to Cite
1. Levdansky V. A., Novikova S. A., Levdanskiy A. V. SULFATION OF BETULIN 3-PROPIONATE WITH SULFAMIC ACID IN N,N-DIMETHYLFORMAMIDE MEDIUM // chemistry of plant raw material, 2024. № 3. P. 280-286. URL: http://journal.asu.ru/cw/article/view/15219.
Issue
No 3 (2024)
Section
Low-molecular weight compounds

Copyright (c) 2024 chemistry of plant raw material

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