TW200538461A - Avermectin and avermectin monosaccharide substituted in the 4"-and 4'-position respectively - Google Patents

Info

Publication number

TW200538461A

TW200538461A TW094106807A TW94106807A TW200538461A TW 200538461 A TW200538461 A TW 200538461A TW 094106807 A TW094106807 A TW 094106807A TW 94106807 A TW94106807 A TW 94106807A TW 200538461 A TW200538461 A TW 200538461A

Authority

TW

Taiwan

Prior art keywords

formula

compound

substituted

group

unsubstituted

Prior art date

2004-04-07

Links

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• 239000005660 Abamectin Substances 0.000 title description 136
• RRZXIRBKKLTSOM-XPNPUAGNSA-N avermectin B1a Chemical compound C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 RRZXIRBKKLTSOM-XPNPUAGNSA-N 0.000 title description 45
• 150000001875 compounds Chemical class 0.000 claims abstract description 343
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 72
• 150000003839 salts Chemical group 0.000 claims abstract description 27
• 239000000126 substance Substances 0.000 claims abstract description 22
• 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 17
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 14
• 239000001257 hydrogen Substances 0.000 claims abstract description 12
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 3
• 239000000203 mixture Substances 0.000 claims description 187
• -1 alkyl nitriles Chemical class 0.000 claims description 150
• 229910052799 carbon Inorganic materials 0.000 claims description 102
• 238000000034 method Methods 0.000 claims description 93
• 125000001424 substituent group Chemical group 0.000 claims description 81
• 238000006243 chemical reaction Methods 0.000 claims description 75
• 125000006239 protecting group Chemical group 0.000 claims description 51
• 125000000217 alkyl group Chemical group 0.000 claims description 46
• 241000607479 Yersinia pestis Species 0.000 claims description 31
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 28
• 125000004429 atom Chemical group 0.000 claims description 28
• 239000002253 acid Substances 0.000 claims description 27
• 239000003153 chemical reaction reagent Substances 0.000 claims description 27
• 125000003342 alkenyl group Chemical group 0.000 claims description 25
• 125000000304 alkynyl group Chemical group 0.000 claims description 24
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 24
• 125000003545 alkoxy group Chemical group 0.000 claims description 23
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 22
• 125000003118 aryl group Chemical group 0.000 claims description 18
• 238000006467 substitution reaction Methods 0.000 claims description 18
• 150000001412 amines Chemical class 0.000 claims description 17
• 238000002360 preparation method Methods 0.000 claims description 17
• 239000004575 stone Substances 0.000 claims description 17
• 239000003085 diluting agent Substances 0.000 claims description 16
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
• 229910052736 halogen Inorganic materials 0.000 claims description 13
• 239000001301 oxygen Substances 0.000 claims description 13
• 239000002689 soil Substances 0.000 claims description 12
• 239000000463 material Substances 0.000 claims description 11
• 230000015572 biosynthetic process Effects 0.000 claims description 10
• 238000003786 synthesis reaction Methods 0.000 claims description 10
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 9
• BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 8
• 239000002841 Lewis acid Substances 0.000 claims description 8
• 125000001931 aliphatic group Chemical group 0.000 claims description 8
• 125000004414 alkyl thio group Chemical group 0.000 claims description 8
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
• 239000007789 gas Substances 0.000 claims description 8
• 125000001072 heteroaryl group Chemical group 0.000 claims description 8
• 150000007517 lewis acids Chemical class 0.000 claims description 8
• XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 7
• 239000000052 vinegar Substances 0.000 claims description 7
• 235000021419 vinegar Nutrition 0.000 claims description 7
• 150000002367 halogens Chemical class 0.000 claims description 6
• XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 5
• 150000003863 ammonium salts Chemical class 0.000 claims description 5
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
• 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 5
• 241000894007 species Species 0.000 claims description 5
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
• 150000002466 imines Chemical class 0.000 claims description 4
• 239000012948 isocyanate Substances 0.000 claims description 4
• 150000002513 isocyanates Chemical class 0.000 claims description 4
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 4
• 125000002524 organometallic group Chemical group 0.000 claims description 4
• PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims description 4
• 125000005907 alkyl ester group Chemical group 0.000 claims description 3
• KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 claims description 3
• 210000000078 claw Anatomy 0.000 claims description 3
• 125000001188 haloalkyl group Chemical group 0.000 claims description 3
• 125000004995 haloalkylthio group Chemical group 0.000 claims description 3
• SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical class ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 claims description 3
• 150000002825 nitriles Chemical class 0.000 claims description 3
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 3
• 239000005046 Chlorosilane Substances 0.000 claims description 2
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
• 125000003277 amino group Chemical group 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims description 2
• 150000002902 organometallic compounds Chemical class 0.000 claims description 2
• 230000004044 response Effects 0.000 claims description 2
• 230000001902 propagating effect Effects 0.000 claims 3
• 235000010290 biphenyl Nutrition 0.000 claims 2
• 239000004305 biphenyl Substances 0.000 claims 2
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
• RHHOPBVKKYWNRH-UHFFFAOYSA-N 1-sulfinyl-2H-pyrene Chemical compound S(=O)=C1CC=C2C=CC3=CC=CC4=CC=C1C2=C34 RHHOPBVKKYWNRH-UHFFFAOYSA-N 0.000 claims 1
• 229960002715 nicotine Drugs 0.000 claims 1
• 210000000952 spleen Anatomy 0.000 claims 1
• 125000004426 substituted alkynyl group Chemical group 0.000 claims 1
• 125000005463 sulfonylimide group Chemical group 0.000 claims 1
• 210000004243 sweat Anatomy 0.000 claims 1
• 125000002947 alkylene group Chemical group 0.000 abstract description 8
• 229910052717 sulfur Inorganic materials 0.000 abstract description 5
• 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 4
• 125000006710 (C2-C12) alkenyl group Chemical group 0.000 abstract 1
• 239000000470 constituent Substances 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 351
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 87
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 85
• 239000002904 solvent Substances 0.000 description 73
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 57
• 150000001721 carbon Chemical group 0.000 description 55
• 229910052757 nitrogen Inorganic materials 0.000 description 52
• 125000004433 nitrogen atom Chemical group N* 0.000 description 49
• 239000000243 solution Substances 0.000 description 49
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 48
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 48
• 238000004587 chromatography analysis Methods 0.000 description 45
• 239000012074 organic phase Substances 0.000 description 45
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 42
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 42
• 229910052938 sodium sulfate Inorganic materials 0.000 description 42
• 235000011152 sodium sulphate Nutrition 0.000 description 42
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 41
• 229910001868 water Inorganic materials 0.000 description 41
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 40
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 34
• 239000002585 base Substances 0.000 description 33
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 31
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
• 239000012071 phase Substances 0.000 description 30
• 241000196324 Embryophyta Species 0.000 description 28
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 27
• 239000000741 silica gel Substances 0.000 description 26
• 229910002027 silica gel Inorganic materials 0.000 description 26
• 229920002554 vinyl polymer Polymers 0.000 description 26
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 25
• 230000014759 maintenance of location Effects 0.000 description 24
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 23
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 23
• 230000000694 effects Effects 0.000 description 23
• 125000000623 heterocyclic group Chemical group 0.000 description 21
• 239000007858 starting material Substances 0.000 description 20
• 239000011550 stock solution Substances 0.000 description 20
• 150000002772 monosaccharides Chemical class 0.000 description 19
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
• 238000012360 testing method Methods 0.000 description 17
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 16
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 15
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
• 239000004480 active ingredient Substances 0.000 description 14
• 235000017557 sodium bicarbonate Nutrition 0.000 description 14
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 14
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 13
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
• 239000000460 chlorine Substances 0.000 description 13
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• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 13
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• 229910052708 sodium Inorganic materials 0.000 description 13
• 239000011734 sodium Substances 0.000 description 13
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 12
• 229910052801 chlorine Inorganic materials 0.000 description 12
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 12
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
• 238000003756 stirring Methods 0.000 description 12
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 11
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• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
• 125000005843 halogen group Chemical group 0.000 description 11
• 229920001223 polyethylene glycol Polymers 0.000 description 11
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