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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

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


Steviosid

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


Steviosid

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


Steviosid

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


Steviosid

M

e

O

M

e

H

M

e

C

O

O

H

2

+

Ratio 2 :1

Molecular complex


Steviosid

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


Steviosid

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.


Steviosid

Supramolecular structure of complex


Steviosid

o-,m-,p-

H

N

2

N

(

M

e

)

2

O

C

H

o-,m-

Me


Steviosid

Resolution of aromatic compounds without active

functional groups

C

H

3

Benzene - toluene

Before resolution

50%

50%

After resolution

20%

80%

NMR, GLC


Steviosid

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


Steviosid

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


Steviosid

2

N

H

NH2

2

N

H

O

N

2

N

O

2

NO2

o-, m-, p-nitroanilines


Steviosid

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


Steviosid

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


Steviosid

A.E.Arbuzov Institute of Organic and Physical Chemistry

Kazan Scientific Centre

Russian Academy of Sciences

_______________________________________________


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