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Новые достижения в химии и химической технологии растительного сырья. Материалы III всероссийской конференции. Книга 2 [2007]

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#"$"& Sweta [3]).

 

O

O

 

 

 

CO2H

 

C

CH2OH

 

 

 

 

 

 

 

 

O

 

 

 

 

 

 

HO

 

 

 

 

 

OH

OH

 

 

 

O

CH2OH

 

O

CH2OH

 

 

 

 

O

 

 

O

 

 

HO

 

 

HO

 

 

 

 

 

 

 

 

 

 

 

OH

 

 

OH

 

 

O

 

O

CH2OH

 

 

CH2OH

 

O

 

 

O

 

 

 

HO

1

 

HO

2

OH OH

 

 

OH

OH

9-+&)$"&<$) %#+,"*A #$+6)$A 6%.+B+1"D++ 5-+1%3+." 2 1"1 , D)-;= <-<2E)*+' )5% 01<,%0A/ 1"2),&0 [4], &"1 + .-' #%+,1" >+%-%5+- 2),1+ "1&+0*A/ ,%).+*)*+4 [5].

9*",&%'?)6 .%1-".) 6A ,%%>?")6, 2&% "-1+-+$%0"*+)6 ,&)0+%-- >+%3+." 2 *)1%&%$A6+ >$%6"-1"*"6+ 0 ,<#)$%,*%0*%4 ,$).) FG!- HI@G >A-+ #%-<2)*A , 0A/%."6+ 20–30% *)+30),&*A) $"*)) 5-+1%-

30

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O

 

 

 

 

C

 

 

 

 

O R

( 3 )

 

 

 

CH2

O

CH2OH

(CH2)2O

( 4 )

O

HO

 

Cl

 

 

 

 

 

 

 

 

O

 

OH

H3C

 

 

CH2OH

 

 

 

O n = 4 ( 5 ), 6 ( 6 )

O

 

(CH2)n N

 

HO

 

N

 

 

OH

O

OH

CH3

 

 

 

96),"+10"+!"# 2 0$1 8+1'C)* D)1+C*$3 -"#(+1"!+3 /6),"+!"#& 1 &*&1+-"C*+ [6], %+6+($E, , /,+F +C)()#2, ,$#)1.1/. "! (&/6)*". Stevia rebaudiana Bertoni &*&1+-"C*+ [7].

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OO

C(CH2)9 C

O

CH2OH

 

HOCH2 O

O

HO

 

 

O

 

 

OH

O

OH

 

OH

O

CH2OH

 

HOCH2

O

 

 

O

 

HO

 

OH

 

OH OH

 

 

7

OH

OH

31

!"#$%'%&

1.!"#$"%&'"() *.+. // !&,-(). $%"/012-''"345. 2004. 612. 7. 61–65.

2.Philips K.C. // Developments in Sweeteners/ Elsevier, London, 1989. V. 1.

3.www.stevian.ru, www.greenlite.ru

4.DuBois G.E., Stephenson R.A. // J. Med. Chem. 1985. V. 28. 61. P. 93–98.

5.Lin L.-H., Lee L.-W., Sheu Sh.-Y., Lin P.-Y. // Chem.Pharm.Bull. 2004. V. 52. 69. P. 1117–1122.

6.Mosettig E., Nes W.R. // Organic chemistry. 1955. V. 20. 67. P. 884–890.

7.8259"'3"( :.8. & #%. // ;<=. 1998. >. 68. 611. 7. 1813–1821.

8.8'#%--() <.:., ?&2&@&') <.A. & #%. // ;<=. 2007, ( $-B)4&.

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: $&,-("C $%"/012-''"34& 34%)' DE'"C 8/-%&F&, DG"- :"34"B'"C 8H&& & I$"'&& ( F)B-34(- '&HF"F)2"%&C'0J H)/-'&4-2-C 3)J)%) 1&%"F" &3$"25HKL43. G2&F"H %)34-'&. Stevia rebaudiana Bertoni [1]. AJ )G2&F"'"/ .(2.-43. #&4-%$-'" (F)K%-'") 34-(&"2 1 (13-G%"F3&-!"#-F)K%-16--'-19-"(). F&32"4)). +)F & (3- (031&- 4-%- $-'", 34-(&"2 1 .(2.-43. M&"2"G&B-3F& )F4&('0/ 3"-#&'-'&-/, $%".(2.L,&/ %)H2&B'0- ( )F4&('"34& (M)F4-%&@'KL [2], )'4&- M)F4-%&)25'KL [3], )'4&("3$)2&4-25'KL & &//K'"/"#K2&%KL,KL [4] & #%.). : 4" E- (%-/. F"2&B-34(" "$&3)''0J ( 2&4-%)4K%- -G" 3&'4-4&- B-3F&J $%"&H("#'0J '- (-2&F". N)/ &H(-34'0 2&15 %)M"40 [2, 5]. :-- %".4'", O4" 3(.H)'" 3 4-/, B4" 34-(&"2 1 ( F&32"C 3%-#- 2-GF" &H"/-%&- HK-43. (M2)G"#)%. ')2&B&L #("C'"C 3(.H& K )4"/) 716 $%"&3J"#&4 $-%-- G%K$$&%"(F) :)G'-%)-?--%(-C')) ( 3("C 34%KF4K%'0C &H"/-% &H"34-- (&"2 2 (!"#-16-F-4"M-C-%)'-19-"(). F&32"4)).

32

18

3

2

1

 

 

 

 

 

 

 

 

 

9

 

 

 

 

H3C

4

 

10

11 15

 

 

 

 

 

 

 

 

 

19

5

 

7

 

16

17

 

 

 

O

6

 

12

CH2

O

 

 

OH

20CH3

 

 

 

 

 

 

 

8

 

 

 

 

 

 

 

 

 

14

13

 

 

OH

 

 

 

 

1

 

OH

 

 

O

 

 

 

 

 

 

 

 

2

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>)'.)*1092 (*"72&"&2+92, ()'/2#$&092 1 82(#*- (."7", 7*#@&0 /0)$ 4.*231*7&0" ()"12*#' 1 /"3 71*-&*- (1+32 ; ')*9' >16. A 8'<"()1" *7&*:* 23 )'826 4.*231*7&06 90 10/.'#2 72:27.*()"12*# (4.*7;8) 1*(()'&*1#"&2+ 71*-&*- (1+32 ()"12*#' 1). A #2)".');." *42('&* 1*(- ()'&*1#"&2" ()"12*#' 1 1*7*.*7*9 &' 4'##'72"106 8')'#23')*.'6 [2], 8*)*.*" 4.21*72) 8 (9"(2 72'()"."*9".*1 (/0#2 .'37"#"&0 8*#*&*<- &*- 6.*9')*:.'?2"-). B0 2(4*#$3*1'#2 7#+ 1*(()'&*1#"&2+ ()"12*#' 1

:27.'32& :27.') 1 4.2(;)()122 &28"#+ C"&"+ 2 4*#;<2#2 ( 106*7*9

20% 4.*7;8), 29"%,2- [D]20D = –40º (( 0.38, CHCl3) 2 ). 4#. = 190 º>.

H3C

CH3

H3C

O OH CH3

O

H

O OH CH3

 

 

3

OH

OH

 

4

 

H3C

CH2OH

 

 

OOH CH3

O

5

>*4*()'1#"&2" &'526 7'&&06 ( #2)".');.&092 [2] 7#+ 16(S)-

72:27.*()"12*#', ' 29"&&*, [D]20D = –28.2 (( 0.43, CHCl3), ). 4#. = 190– 192 º>, 2 7#+ 16(R)-72:27.*()"12*#', ' 29"&&*, [D]20D = –110.9 (( 0.33, CHCl3), ). 4#. = 216–218 º>, 4*8'3'#*, <)* &'92 /0# 4*#;<"& 16(S)-

33

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H3C

 

 

 

H C

 

 

 

 

 

 

CH2OH

3

 

CH NH(CH ) OH

O

 

 

 

O OH CH3

2

2 3

OH CH3

OH

OH

OH

 

 

6

 

 

7

OH

 

H3C

 

 

 

 

 

 

 

CH2NH(CH2)3OH H C

 

 

 

 

 

 

 

 

 

O

 

 

OH

3

 

CH2NH(CH2)3OH

NH CH3

 

 

 

 

O

OH CH3

 

 

 

(CH2)3

OH

 

 

 

 

 

 

O

 

 

8

 

 

9

 

OH

 

 

 

 

 

 

 

 

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H3C

 

H3C

 

 

H3C

 

 

O

Br2

 

CH2Br

 

CH2Br

O OH CH3

O

 

O

 

isoniaside

OH CH3

 

OH CH3

 

OH

 

O

 

O

 

 

 

Br

 

 

 

 

4

 

 

10

 

 

11

 

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35

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H3C

 

 

 

 

 

PhCH2Br

O

O

 

 

CH2

 

 

CH3

 

 

 

 

CH2

 

( 12 )

 

 

 

 

OH

 

 

 

 

 

H3C

 

 

 

 

 

 

O

CH2

 

CH2

 

 

CH2

 

OH CH3

 

 

OH

HO

 

OH

 

 

 

 

 

 

 

 

 

( 1 )

 

 

 

 

 

 

Br(CH2)9Br

 

CH3

 

H3C

 

 

 

 

 

 

 

O ( CH2 ) 9

O

 

 

CH3

O

 

 

O CH3

( 13 )

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!"#$%'%&

1.>$+!$"#)$*2 F.=. // >#&'*2: !"$3,G('))$6%/. 2004. H12. I. 61–65.

2.Pezzuto J.M. et al. // Proc. Natl Acad. Sci USA. 1985. V. 82. P. 2478–2482.

3.Lin L.-H., Lee L.-W., Sheu Sh.-Y., Lin P.-Y. // Chem.Pharm.Bull. 2004. V. 52. H9. P. 1117–1122.

4.Boonkaewwan, C. et al. // J.Agric.Food Chem. 2006. V. 54. P. 785–789.

5.Avent A.G. et al. // J. Chem. Soc. Perkin Trans 1. 1990. P. 2661–2665.

6.www.stevian.ru, www.greenlite.ru

7.J(/1$)6$* 4.J. # +". // KLM. 1998. A. 68. H11. I. 1813–1821.

8.?23'+$* 4.J. # +". // KLM. 2005. A. 75. I. 622–628.

9.J)+"''*2 L.4. # +". // KLM. 2007, * !'72%#.

36

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H

 

 

H

 

 

 

H

 

O

OH

 

O

OH

 

 

 

 

 

 

O

OH

 

 

 

 

 

H

 

 

H

 

 

 

 

CH2OH

 

CH2OR

 

 

 

 

 

 

 

 

H

 

 

 

 

 

 

 

N3

 

H

 

 

H

 

 

 

 

 

 

 

 

 

 

 

H

HO

O

 

HO

O

 

 

 

 

 

 

 

 

HO

O

H

 

 

H

 

 

 

 

 

 

 

 

 

 

H

 

 

 

 

 

 

 

 

 

 

O

 

 

O

 

 

 

 

O

 

OH

 

 

OH

 

 

 

 

 

H2C

H O

 

H2C

H O

 

 

 

OH

 

H

TosCl

H

 

 

NaN3

H2C

H O

 

 

 

 

H

O

 

O

O

 

 

O

 

 

OH

OR

 

 

O

O

 

 

 

 

 

 

 

 

 

 

 

 

 

OR

H

H

 

H

 

H

 

 

 

 

 

 

 

H

H

 

 

n

 

 

 

 

n

 

 

 

 

 

 

 

n

 

 

 

Tos = H3C

 

 

S O2

 

 

 

R= H or Tos

37

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1.Liu C., Baumann H. // Carbohydrate research. 2002. V. 337. P. 1297–1307.

()*+,-!!*./+(-0 +,)1(,1)- -2*!*3- 3/4*3)5-6*/,*25758 (*+!5,9

:&; +<;=">1, +;>? 3@$>(A&>1, -.6. )&BC"DE 2, 6.-. )&BC"DE 2

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38

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39

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