Design, synthesis and bioactivity studies of novel sugar derivatives
131
0
0
Texte intégral
(2) N° ENSC-2008/. THESE DE DOCTORAT DE L’ECOLE NORMALE SUPERIEURE DE CACHAN ET DE L’EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY Présenté par Monsieur Chenjiang ZHU Pour obtenir le grade de DOCTEUR DE L’ECOLE NORMALE SUPERIEURE DE CACHAN ET DE L’ L’EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY Domaine : CHIMIE Sujet de la thèse :. Conception, synthèse et étude biologique des nouveaux dérivés de sucre Thèse présentée et soutenue à Shanghai le 4 novembre 2008 devant le jury compose de :. Catherine Kadouri Jie Wu Pierre Audebert Xiaoxin Shi Guo-Rong Chen Joanne Xie. Chargée de Recherche au CNRS Professeur des Universités-Fudan University Professeur des Universités-ENS Cachan Professeur des Universités-ECUST, Shanghai Professeur des Universités-ECUST, Shanghai Professeur des Universités-ENS Cachan. Rapporteur Rapporteur Examinateur Examinateur Directrice de thèse Directrice de thèse. Photopysique et Photochimie Supra- et Macromoléculaires (PPSM/UMR8531/ENS CACHAN) 61, avenue du Président Wilson, 94235 CACHAN CEDEX (France) Institute of Fine Chemicals (East China University of Science and Technology) 130 Meiling Road, Shanghai 200237, P. R. China.
(3) Acknowledgments. I would express my thanks to my supervisor, Prof. Guorong CHEN and Prof. Joanne XIE, they gave me lots of important suggestion, thanks for French government, they gave me the bourse de Eiffel to support my study career in France, thanks for Lab PPSM (Laboratoire de Photophysiquee Photochimie Macromoléculaires et Supramoléculaires) ENSC (Ecole Normale Supérieure de Cachan, France), support a good condition for research.. Thanks for researchers in the lab PPSM, Mr. Stephane Maisonneuve, Mr. Arunaud Brosseau, and thanks for Jia LI and Jianwen LIU, they tested the bioactivities of all compounds. Of course, I thanks for my workmates Li LIN, Kelly CHENG, Xiaopeng HE and all of people who once helped me..
(4) .
(5)
(6)
(7)
(8)
(9) . .
(10)
(11)
(12) . .
(13)
(14)
(15)
(16)
(17)
(18) . .
(19)
(20) . . . .
(21)
(22) . . !"# $ %!&'! . ( . ) !"# $ *!&'! . + . !",* $-$ .! . + . / !",. $, -$ .! $ %!&'! . 0 . ( 1*! . !!" *!2 $-*!'1. 3 . + 1 . *,$,,$ . 3 . 0!,. 4 . 5.
(23)
(24) . .
(25)
(26) . . ( !".!#1!'). /. () !".!#1!' . /. ( !".!#1!'/. (. (/ !".!#1!'+. (. (( !".!#1!'0. +. (+ !".!#1!'3. +. (0 !".!#1!'5. +. . .
(27) . (3 !".!#1!'. 0. (6 !".!#1!'). 0. (5 !".!#1!'/. 3. ( !".!#1!'+. 3. () !".!#1!'3. 3. ( !".!#1!'6. 6. (/ !".!#1!')5. 6. (( !".!#1!'). )5. (+ !".!#1!')). )5. (0 !".!#1!') . ). (3 !".!#1!')/. ). (6 !".!#1!')(. )). ()5 !".!#1!')+. ) . () !".!#1!')0. ) . ()) !".!#1!')3. )/. () !".!#1!')6. )/. ()/ !".!#1!' 5. )(. ()( !".!#1!' . )(. ()+ !".!#1!' ). )+. ()0 !".!#1!' . )0. ()3 !".!#1!' /. )0. ()6 !".!#1!' (. )3. ( 5 !".!#1!' +. )3. ( !".!#1!' 0. )6. ( ) !".!#1!' 3. )6. . .
(28) . ( !".!#1!' 6. 5. ( / !".!#1!'/5. 5. ( ( !".!#1!'/. . ( + !".!#1!'/). . ( 0 !".!#1!'/ . ). ( 3 !".!#1!'//. . ( 6 !".!#1!'/(. . (/5 !".!#1!'/+. /. (/ !".!#1!'/0. /. (/) !".!#1!'/3. (. (/ !".!#1!'/6. (. (// !".!#1!'(5. +. (/( !".!#1!'(. +. (/+ 21 *# ,$1*!. '* "!* *! , . 0.
(29) . .
(30)
(31)
(32)
(33) . .
(34)
(35) . .
(36)
(37) . .
(38)
(39) . . )/ !".!#1!'( . //. )/) !".!#1!'((. /(. )/ !".!#1!'(+. /(. )// !".!#1!'(0. /+. )/( !".!#1!'(3. /+. . .
(40) . )/+ !".!#1!'(6. /0. )/0 !".!#1!'+5. /0. )/3 !".!#1!'+. /3. )/6 !".!#1!'+). /3. )/5 !".!#1!'+ . /6. )/ !".!#1!'+/. (5. )/) !".!#1!'+(. (5.
(41) . .
(42)
(43) . . . .
(44)
(45) . . .
(46) . !.
(47) . !. '-,*. (+. ) 1 ! !$,$ -*!'1. (0.
(48)
(49)
(50) . . ( 1 ! ! 1*! . !. (6. +#!"., !!",!# *.# $-*!'1. +5.
(51)
(52) . ! . ) !"/ +!7)8 *!9 % $ α# $-$ .!1 *,! . +. )( !# *%, !. +0. )+ !" :1 ! !. *!#.#!$ .'$ . +6. )0α,$$ $, !!"! *! % $1*! . -$ .! . 05.
(53)
(54) . " .
(55)
(56) . " . . 4.
(57) . / !".!#1!'+0. 0. /) !".!#1!'+3. 0). / !".!#1!'+6. 0 . // !".!#1!'05. 0 . /( !".!#1!'0. 0/. /+ !".!#1!'0). 0/. /0 !".!#1!'0 . 0(. /3 !".!#1!'0(. 0+. /6 !".!#1!'0+. 0+. /5 !".!#1!'00. 00. / !".!#1!'03. 00. /) !".!#1!'06. 03. / !".!#1!'35. 03. // !".!#1!'3). 06. /( !".!#1!'3 . 06. /+ !".!#1!'3/. 35. /0 !".!#1!'3(. 35. /3 !".!#1!'30. 3. /6 !".!#1!'33. 3. /)5 !".!#1!'36. 3). /) !".!#1!'65. 3). * " * . . 3.
(58)
(59)
(60)
(61)
(62)
(63) . .
(64)
(65)
(66)
(67)
(68)
(69)
(70) . . . 4.
(71) . . !. / .$.;. # * "!* .! . ! : ,#!,. , '-,*. 36.
(72)
(73) . # . /) !",%!,. . 6. /)) $ $, !!"# $α-$'.!1 *,! . 6. /) !"-$ .! "!. !,$% : 1*!1,*- $ *. 6(. /)/.$.;* ,. !. 6+. /)( ! "!*1 1. 63.
(74)
(75) . . // !".!#1!'6/. 5). //) !".!#1!'6+. 5 . // !".!#1!'63. 5 . /// !".!#1!'66. 5/. //( !".!#1!'55. 5/. //+ !".!#1!'5. 5(. //0 !".!#1!'5). 5(. //3 !".!#1!'5 . 5+. //6 !".!#1!'5/. 5+. //5 !".!#1!'5(. 50. // !".!#1!'5+. 50. //) !".!#1!'50. 53. // !".!#1!'53. 56. /// !".!#1!'5. 56. //( !".!#1!'. 5. //+ !".!#1!'). 5. . 4.
(76) . //0 !".!#1!' . . //3 !".!#1!'/. . //6 !".!#1!'(. ). //)5 !".!#1!'+. ). //) !".!#1!'0. . //)) !".!#1!'3. /. //) !".!#1!'6. /. //)/ !".!#1!')5. (. //)( !".!#1!')). (. //)+ !".!#1!') . +. //)0 !".!#1!')/. 0. * . . . . . . . . . . 4. . . . . . . . . 3.
(77) . . $%&'()*(+,$%&%-(.&/-0+&1&+*+2.&$%/3
(78) /1$42'-5$5&1-+&1$% 6%+5-0+. < =
(79)
(80)
(81)
(82) > ?
(83) @ >
(84) A
(85) AA>
(86) A>
(87)
(88) A @
(89)
(90)
(91) @
(92)
(93) @A
(94) A
(95) A
(96) #<
(97)
(98) A
(99)
(100)
(101)
(102) AB ,A
(103) >@
(104)
(105)
(106)
(107)
(108) A><
(109) CD
(110) @
(111)
(112) <
(113) EF ,@
(114) ?
(115) >
(116) A
(117)
(118) >>
(119)
(120)
(121) A
(122) A>
(123)
(124)
(125) <?
(126) @ A @
(127) <
(128) C+<A> @ >> @
(129)
(130) A> A
(131)
(132)
(133) @
(134)
(135) 55GHA$ A> <
(136) A @
(137) @
(138)
(139) )55 GHA$ < A> @
(140)
(141)
(142) I@
(143)
(144)
(145)
(146) 7/55GHA$9 E)F 4
(147) A
(148) A
(149) A>
(150)
(151)
(152) =
(153) >
(154) <? A
(155) A <
(156) C A
(157) @A
(158) =A> @>
(159) E F @ > >
(160)
(161) A
(162) >@A
(163) @
(164)
(165)
(166)
(167)
(168)
(169)
(170)
(171)
(172) <?
(173) ?><
(174)
(175) >
(176) @ @ >8 @ @?
(177) > / +!7
(178) 9@C <
(179)
(180) " J
(181) )! +!7
(182) 9@C >
(183)
(184) > <
(185) C
(186) (<A>>
(187) E/F @
(188) #
(189) )
(190)
(191) 1
(192)
(193) > >
(194) >
(195)
(196)
(197)
(198)
(199)
(200)
(201) @
(202) A @
(203) C >
(204)
(205) @
(206) 1 1 ,? C <
(207) ? A
(208)
(209) A
(210) ,A
(211)
(212)
(213) A
(214)
(215) <3 /K @
(216) 1 1
(217) ( GHA$ $*7/5.%8 > 1
(218) @ 1
(219)
(220) -> 1 1 ,A ,@
(221) 4
(222) A
(223) . .
(224) . $($5-4(+5/.20+&/(.
(225) @
(226) @
(227)
(228)
(229)
(230)
(231) <
(232)
(233) <? A " .@
(234)
(235)
(236) <
(237)
(238) 6 5@ <
(239) .@
(240) @ >>
(241) @
(242)
(243) AA
(244) A
(245)
(246) >>
(247) A>=
(248)
(249) @
(250) A
(251) @
(252) <
(253)
(254) >
(255) )55 > @
(256)
(257) < >@ LM
(258)
(259)
(260) N.O
(261)
(262) A <?@
(263)
(264)
(265)
(266) <
(267)
(268) @<
(269)
(270) A>
(271) P)$? A @
(272)
(273) OA
(274) >
(275)
(276)
(277)
(278)
(279)
(280) @
(281)
(282) @
(283) ? @@>
(284)
(285) AA> ,
(286) <
(287)
(288) <?<
(289) @
(290)
(291) <
(292)
(293) @> A
(294) @ > . A
(295) @ A
(296) > < A
(297)
(298) >
(299) C @
(300) A
(301)
(302) A>=>
(303) >
(304)
(305)
(306)
(307)
(308)
(309) =>
(310) >
(311)
(312) A
(313)
(314) AB
(315) A
(316)
(317) A@ A
(318) @ A
(319) @
(320)
(321)
(322)
(323)
(324)
(325)
(326)
(327)
(328)
(329)
(330) A
(331) @A Q
(332) ,B
(333) 4?/
(334) N
(335)
(336) <
(337)
(338)
(339) P. . ).
(340) . . ,-9+$5 *(+,$%&%/3
(341) /1$4562+&('4*0/%&.$$5&1-+&1$% 3/5(,&6&+&/(/3*5/%&(-%$ (+5/.20+&/( ,@
(342) / > > <
(343)
(344) ><
(345)
(346) A
(347) >
(348) (,@
(349) A>
(350)
(351)
(352) A@ >
(353)
(354) A @ "
(355) A @
(356) @
(357)
(358) A >A
(359) <
(360) C
(361) >
(362) A
(363) >A
(364) A
(365) @ =
(366) +# @
(367) @
(368)
(369) <
(370) ?+
(371)
(372)
(373) @
(374)
(375) > @
(376)
(377) A I@
(378) A<
(379) ?
(380) ,
(381)
(382)
(383)
(384) @A
(385)
(386) @
(387) @
(388)
(389)
(390) A <
(391) @
(392) 0 '4*0/%&.$ ,
(393) Q @
(394)
(395) @
(396) > <
(397) @
(398)
(399) .. @
(400) > C A3 6
(401) @ > A >
(402)
(403)
(404) A
(405)
(406) ? @
(407) >>
(408)
(409) 5 . A. @
(410)
(411) @
(412)
(413)
(414)
(415) > "=A> ;*0555 A
(416)
(417) R
(418)
(419)
(420)
(421) A
(422) > 6@@ ;C?<? )>>
(423)
(424)
(425)
(426) A
(427)
(428) +@A Y Z HO. O. OH. m NH. O X OH. R OH. OH. KRN7000,X=O,Y=OH,Z=H,m=20,R=. 10. . " A>
(429) @
(430)
(431)
(432) @
(433) # *B . /
(434) C
(435) @ S.
(436) ;*0555)55/
(437)
(438) A
(439)
(440)
(441) <
(442)
(443) 4
(444) ? *
(445) <
(446)
(447)
(448) @
(449)
(450)
(451) @
(452)
(453) . .
(454) . . @ A> OH. OH. O HO. O NH. OH. OH. . OH. .;*0555 <? . @
(455) <
(456) C
(457) A
(458) A..@
(459) C. <@<O. > <? < >>>
(460)
(461) ( +
(462) C
(463) . @
(464)
(465)
(466)
(467)
(468) <O. HO HO. OH HO HO. OH R 1 O. R2. OH O HO. R3. HO OH. * *) * T . . . /. OH O HO. OH R1 O HO. R2 R3 OH. .
(469) OH. O. R1. R2. R1. R2. R3. R3 O OMe. OH R1. R2. R1. R2 OMe R3. R3. O. OMe. OH. R1. R2 R3. OAc OH O. R HO. R AcO. OH HO. OAc AcO. OH. OH O. R1. R2. O. R3. OH. OMe. OAc O. R1. O R2. O. R3. OAc. R1. R3. OAc. OH. OH. R2. O. .
(470)
(471)
(472) @
(473) $%24+%-(..&%02%%&/( . *(+,$%&%/3:$+,*46$(;/<2&(/($ O. OH R. R. Fremy's salt. R. R R. R O. . *T . A A
(474)
(475) C @CQ #
(476) "A U
(477) 7; ! 9)!
(478) =
(479) > AA ?
(480) >
(481) A
(482) AA
(483) >>
(484) "A U
(485)
(486) A
(487)
(488)
(489) AA<
(490) <@
(491) 5V)5K > @
(492) @
(493) <35D
(494) 65K >
(495) @ =
(496)
(497) ><
(498)
(499)
(500) >
(501) . . (.
(502) . . *(+,$%&%/3:$+,*4,*.5/<2&(/($ OH. O R. R. Na2S2O4. R. CHCl3 / H2O. R. R R OH. O. . : ) )!/
(503)
(504) @C Q . . H )!
(505) A
(506) A>
(507) ,
(508) 5A A
(509)
(510)
(511) A
(512) @A
(513)
(514)
(515) > A <
(516) <
(517)
(518) AQ?
(519)
(520) 65K
(521) >
(522) @=
(523)
(524) ><
(525)
(526)
(527) >
(528) . *(+,$%&%/3-5*4'4*0/%&.$ AcO O OAc. R1 +. OCH3 R2. AcO SnCl4 / AgOTf CH2Cl2. R3. OAc. O. OCH3 R2. R1. R3 OCH3. OAc. OCH3. . ? ;@ 0 >
(529) A
(530) $< ,!
(531)
(532)
(533)
(534) C.
(535) ".
(536)
(537)
(538) A AA
(539) @<O AcO. AcO. M + Ln-. O. AcO. AcO. AcO. CH3. OCH 3. AcO. O. AcO OAc. AcO. O. O. AcO AcO. AcO. AcO OCH 3. O. . CH3. :
(540)
(541)
(542)
(543) A>
(544) A>
(545)
(546)
(547)
(548)
(549)
(550)
(551)
(552) <<
(553) AAC
(554)
(555) @O. AcO AcO. OAc O. OMe OAc O. AcO O AcO. + OAc. AcO 18. AcO AcO. OMe OAc O. AcO O AcO. OMe. AcO. 4. OMe. 27. OMe. AcO AcO. OAc O OMe AcO O AcO. OMe. OAc O AcO. 8. . OAc O. 38. +. OMe. .
(556) .
(557)
(558) - > A
(559)
(560) A>
(561) 5/.20+ $:9$5-+25$7 9 )5 " )( " 5 " ( " = " )5 )( 5 ( = . -+$5&-4% . &$4.= 0 /( + (/ () /5 ( + +0 +. .
(562)
(563) @ @
(564)
(565) ( W. <
(566) ) / +>
(567)
(568) > 75Q9<
(569) /A
(570) = ) (A
(571) @C 7)5Q9 A=
(572) αβA<
(573) 0K OMe. OMe AcO AcO. OAc O OAc. AcO AcO. +. OAc O OAc. OAc. OMe. OMe. 14. 12. AcO AcO. OAc O OAc OMe. MeO. . >
(574)
(575) A=
(576)
(577)
(578)
(579) < < 8
(580)
(581) C
(582)
(583) > . *(+,$%&%/3-0$+*4-+$.'4*0/%*46$(;/<2&(/($ AcO. R1 O OAc. OCH3 R2 R3. O AcO CAN CH3CN / H2O. OCH3. R1 O OAc. R2 R3 O. . ., =
(584) A
(585) = @C
(586) AQ? A A3<O . 0.
(587) . R1. OCH3 R2 2 Ce4+ + 2H2O*. + R3. H3CO O*H R2 R1 R4 R3 H*O OCH3. R4 OCH3. + 2H+. + 2Ce3+. O* R1. R2 + 2CH3OH. R3. R4 O*. . !X
(588) >! . $95/+$0+&/(/3,*.5/>*4'5/29 OH. OH AcO. R1 O OAc. R2. OH R1 O. R3. OH. R2 R3 OH. OH. . ,>>?< A
(589) @C@
(590) A !#H#! A
(591) AA @
(592) . .!.H#!
(593) ,
(594)
(595) <
(596)
(597) A
(598) @
(599) @
(600)
(601)
(602) < OH AcO O. R1. OAc. OH. HO. R2. CH3ONa. R3. MeOH. O. R1. R3. OH. OH. R2. OH. . <
(603)
(604) A
(605)
(606)
(607) >
(608) OH AcO O. R1. OAc. !. OH. HO. R2. CH3COCl. R3. MeOH. O OH. OH. R1. R2 R3 OH. . 9$0+5-4-(-4*%&% . " A> ) 1$. <
(609) > A
(610) 6(K @
(611)
(612) #* >
(613) @
(614)
(615)
(616) A> #A
(617) #*>
(618) . 3.
(619) . AcO AcO. OCH3. OAc O. AcO AcO. AcO. OAc O. OCH3. AcO. OCH3. OCH3. 19. 30. . :
(620)
(621) A?>
(622) A>
(623)
(624)
(625) A>
(626) O)( (5 65
(627) <O!
(628) . @ (5 . . 6.
(629) . 65 . #*>
(630) A>
(631) )( (5 65 . >
(632) A>) A
(633)
(634)
(635) A> A @
(636)
(637) =
(638)
(639)
(640) A>
(641) #O . OAc AcO. OAc O. OCH3. AcO AcO. OAc O OCH3 AcO O AcO. AcO. OAc O AcO. OCH3. 38. 34. #. OCH3. . . ". &/-0+&1&+*. *
(642) @
(643) @
(644)
(645) <
(646) ?1>>@ <
(647) ?
(648) 8 A>
(649)
(650)
(651)
(652)
(653) . 5.
(654) .
(655) <
(656) ?,<?<
(657) AA >@
(658) @
(659)
(660) @
(661)
(662) A @
(663) < <? ,$+*5/%&(-%$&(,&6&+&/(5$%24+ (,&6&+&/(5-+$K /:9. ?'@: ?'@: ?'@: ?'@: *.5/<2&(/($ 9$(+--0$+*4A'420/%$ 9$(+--0$+*4A'-4-0+/%$ A'420/%$ A'-4-0+/%$ B-562+&( A-562+&(. ) ( (33 3)0 66 53/ +) ))6. )563 6)3 )3 0)5 5 ( )6/6 ) ). )533 ( 0 5/ 0(+ 565 5 )5/ . 5 5 5 5 5 5 5. /05). )0 +. (5(. 5. +(. 3 5. )/. 5. 6. /3. /03. 5. )(65. )0(). )0. 5. ( /. 36. 0/). 5. OH OAc O. AcO AcO. AcO OH . OH AcO AcO. OAc O AcO OH. . OH AcO AcO. OAc O AcO OH. . OH. OAc AcO. OAc O. AcO OH . " OAc AcO. OH OAc O. AcO OH. . .
(664) . ! OH. OAc AcO. OAc O. / . )6 . . 5. )(). )+5. 5 +. 5. 663. )) 3. 6 /. 5. 0/+. () . ) /. 5. ))+3. ) 65. )(+. 5. )+5+. )(60. )/(. 5. AcO OH. . OH OH O. HO HO. HO OH. . OH OH O. HO HO. HO OH. . OH OH O. HO HO. HO OH. . OH. OH HO. OH O HO OH. . OH HO. OH OH O HO OH. . ". . ).
(665) . OH. OH HO. OH O HO OH. 36/. 6)/. / 3. 5. +5 . )0/. 3/0. 5. /56. 5/6. / . 5. 53. /3. /). 5. . ! AcO AcO. OAc O AcO. OH OAc O. O AcO. AcO. OH. . AcO AcO. OAc O AcO. OH OAc O. O AcO. AcO. OH. AcO AcO. OAc O AcO. OH OAc O. O AcO. AcO. OH. # /(042%&/(
(666) >
(667) <? <
(668)
(669) A> <
(670) @
(671)
(672) <
(673)
(674)
(675)
(676) @
(677) @@
(678) <
(679) C/( . @
(680) +
(681) A<A> @
(682)
(683) A> A
(684)
(685)
(686) @
(687)
(688) 55 GHA$ A> <
(689) A @
(690) @
(691)
(692) )55 GHA$ < A> @
(693)
(694)
(695) I@
(696)
(697)
(698)
(699) 7/55 GHA$9
(700) >
(701)
(702) @
(703) >
(704)
(705) <
(706)
(707) <
(708)
(709) . . .
(710) . >9$5&:$(+-4%$0+&/( . *(+,$%&%/30/:9/2(. O. OH Fremy's salt. O. . . ). 9 >>
(711) "A U
(712)
(713) !)75 5/(A9)5A$ )! ) )!(7( 55+A9 5A$ )!<><
(714) @
(715)
(716) (A +A$. .!) <
(717)
(718)
(719) <
(720) 5A
(721) )5A$AA7+#9< < @ >< 7 5 A9 ;#!/ 7/) 55)+A9 55 A$ )!
(722) A=
(723) <
(724)
(725)
(726)
(727) <
(728)
(729) Q;.55A$
(730) 5 A
(731)
(732)
(733) ?"A 8
(734) )9
(735) A>
(736)
(737)
(738) "A 8
(739) 7@
(740) @9)55A$ )! ) A
(741) > 7/( +33AA9)55A$#! <><,
(742)
(743)
(744) A=
(745) <
(746)
(747) A
(748) A>
(749)
(750) $. <
(751)
(752)
(753) A
(754) <AA>
(755)
(756)
(757)
(758) <=
(759)
(760) <
(761) . ).)7 Y55A$9 A@ < < <
(762) @ # !/ >
(763) > <
(764) A A
(765) > 7.#O>
(766) A
(767) T O 9
(768) A> 7/+) 6)K9 < $.O T5/6 71
(769) O
(770) !,T O9D #* 7)(5 # C .. 9O 6)7 + )Y. 9 ++7 ) 1 9 . *(+,$%&%/30/:9/2(. OH. O Na2S2O4 CHCl3 / H2O. OH. O. . . .
(771) A>7 + 5AA9. . 5A$ ) )!/75/ +5AA9 )!7 5A$9<
(772) A=
(773) <
(774)
(775)
(776) A
(777) A>
(778) /( . /.
(779) . A >
(780) <>
(781)
(782) <
(783)
(784) )!7 Y)5A$9 )!7 5A$9 A@ < < <
(785) @ # !/ >
(786)
(787) A> 7 6(K 9 <
(788) $.O T5)0 71
(789) O
(790) !,T O9D #* 7(55 # C .. 9O ) 7 + )Y1 . 9 /() 7 ! 9 /6) 7 ! 9 + ) 7 ) 1 9 *(+,$%&%/30/:9/2(. OCH3. OH CH3I KOH DMSO. OCH3. OH. .
(791) A>7 3 5AA9# !73A$9 ;7 )A$ (5AA9< ><
(792) A
(793) A>
(794) <@ ;! 7/ 05AA9,
(795)
(796)
(797)
(798)
(799) <
(800) (
(801)
(802) <
(803) <
(804) )! 7)5 A$9 =
(805)
(806) <
(807) . ).) 7 Y 5 A$9 A@ < < <
(808)
(809) Q ) )! @ # !/ >
(810) > <
(811) A A
(812) > 7>
(813) A
(814) O
(815) !,T O9
(816) A> 7() 6)K9 <
(817) $.O T5(671
(818) O
(819) !,T O9D #*7(55# C .. 9O )37 + )Y1 . 9 067 + )Y!. 9 ++37 ) 1 9 . *(+,$%&%/30/:9/2(.! O. OH Fremy's salt. O. . ! )5"A 8
(820) 55A$<
(821) A>7/( 0AA9#! 7/55 A$9 < ><
(822) /
(823) A
(824) A>
(825) =
(826)
(827) <
(828) . ).) 7 Y55A$9
(829) A@ << <
(830) @ # !/ >
(831) > <
(832) A A
(833) > 71
(834) O
(835) !, T O9
(836) A> ! 7/3 6(K9 <
(837) $.OT5()71
(838) O
(839) !,T O9D #*7(55# C .. 9O )5(7 + T+3 C )Y1 . 9 +(+7 ) 1 9. . (.
(840) . . *(+,$%&%/30/:9/2(." O. OH Na2S2O4 CHCl3 / H2O. O. OH. . ! " A>!7 + 5AA9 5A$. . ) )!/75/ +5AA9 )!7 5A$9<
(841) A
(842) A>
(843)
(844) A=
(845) <
(846) /(A >
(847)
(848) A
(849) < >
(850)
(851) <
(852)
(853) )! 7 Y)5 A$9 )! 7)5A$9
(854) A@ << <
(855) @ # !/
(856) A>"7)0 6)K9 $.OT5671
(857) O
(858) !,T)O9D #*7(55# C # ! 9O ))57 + )Y1 . 9 /))7 ! 9 /)37 ! 9 +/37 ) 1 9 ! *(+,$%&%/30/:9/2(. . . OH. OCH3 CH3I. KOH. DMSO OH. OCH3. . " A> " 7 3 5 AA9 # ! 73 A$9 ; 7 ) A$ (5 AA9 < ><
(859) A
(860) A>
(861) <@ ;! 7/ 05AA9,
(862)
(863)
(864)
(865)
(866) <
(867) (
(868)
(869) <
(870) <
(871) )! 7)5 A$9 =
(872)
(873) <
(874) . ).) 7 Y 5 A$9
(875) A@ < < <
(876)
(877) Q ) )! @ # !/ >
(878)
(879) >
(880) > <
(881) A A
(882) > 7>
(883) A
(884) O
(885) !,T O9
(886) A> 7(5 65K9<
(887) $.O T5(71
(888) O
(889) !,T)O9D #* 7(55 # C .. 9O ))( 7 + )Y. 9 +(7 !. 9 07 !. 9 +( 7 ) 1 9 " *(+,$%&%/30/:9/2(. O. OH Fremy's salt. O. # . +. .
(890) . )5"A 8
(891) 55A$<
(892) A>#7/( 0AA9#! /55 A$ < ><
(893) /
Documents relatifs
