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Steviosid

Plant Stevia rebaudiana Bertoni. 0. mp. =. 2. 0. 1. -. 2. 0. 3. С. 2. 0. 0. a. ]. [. =. -. 3. 9. 3. (. H. O. ,. C. 5. 7. ). D. 2. HBr,H 2 O. Isosteviol. Steviosid. 17. M. e. 12. 13. 11. 16. 20. O. 16. C. M. e. 14. D. 9. 1. Me. 10. 2. 8.

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Steviosid

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  1. Plant Stevia rebaudiana Bertoni 0 mp = 2 0 1 - 2 0 3 С 2 0 0 a ] [ = - 3 9 . 3 ( H O , C 5 . 7 ) D 2 HBr,H2O Isosteviol Steviosid

  2. 17 M e 12 13 11 16 20 O 16 C M e 14 D 9 1 Me 10 2 8 Me A B 5 7 3 4 6 15 O O H H Me O 19 18 M e C 2 1 O O H a b b (4 , 8 , 13 )-13- methyl-16-oxo-17-norcauran-18-carbonic acid ISOSTEVIOL

  3. 17 M e 12 13 11 16 20 O 16 C M e 14 D 9 1 Me 10 2 8 Me A B 5 7 3 4 6 15 O O H H Me O 19 18 M e C M e 2 M e 1 O O H O M e Y X Me Me Me Me Me Me Me Me Me Me Me Me Y O M e OR Me O O O O O O OR OR OR OR Cl NR2 Me Me Me Me Me O O O O NR M e M e Hal

  4. 17 M e 12 13 11 16 20 O 16 C M e 14 * D 9 * * 1 Me * * 10 2 8 Me A B * 5 7 3 4 6 15 O O H H Me O 19 18 M e C 2 1 O O H a b b (4 , 8 , 13 )-13- methyl-16-oxo-17-norcauran-18-carbonic acid ISOSTEVIOL Individual stereoisimer (enantiomer) (R)-C4, (S)-C5, (R)-C8, (S)-C9, (S)-C10, (S)-C13

  5. M e O M e H M e C O O H 2 + Ratio 2 :1 Molecular complex

  6. O R C O H H H N P h N H H O R C O H O O R C H R C N R 3 O H N R O 3

  7. Dimer of Pure Isosteviol in Crystal. X-Ray data Dimer of Isosteviol in Complex’s Crystal. X-Ray data O O H O O H O O O H O O O H O O Lossin Energy is more than 12 kcal/mol. PM 3 Method. HyperChem 6.0.

  8. Supramolecular structure of complex

  9. o-,m-,p- H N 2 N ( M e ) 2 O C H o-,m- Me

  10. Resolution of aromatic compounds without active functional groups C H 3 Benzene - toluene Before resolution 50% 50% After resolution 20% 80% NMR, GLC

  11. C H 3 C H 3 C H 3 H C 3 H C C H 3 3 C H C 2 Resolution of aromatic regioisomers o,m,p-xylenes, ethylbenzene. Before resolution 26% 56% 18% After resolution 42% 54% 4% H 3 NMR, GLC

  12. N H 2 N O 2 O O N N N N H H 2 2 2 2 N H 2 O N 2 Resolution of aromatic regioisomers o-, m-, p-nitroanilines After resolution 100% 0% 100% 0% Before resolution 50% 50% 50% 50% NMR, GLC

  13. 2 N H NH2 2 N H O N 2 N O 2 NO2 o-, m-, p-nitroanilines

  14. Enantiomers’ resolution R R S OH O H H O O H H H H M Me e M e H R M e R In solution In crystal R [a] Pure Isosteviol - 81о Complex with Phenylmethylcarbinol - 31о

  15. si-attack Nu O si-attack Nu H O H si-attack Nu O O H si-attack Nu H S Chiral nanosize molecular reactor

  16. A.E.Arbuzov Institute of Organic and Physical Chemistry Kazan Scientific Centre Russian Academy of Sciences _______________________________________________

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