JPS58170797A

JPS58170797A - オリゴサッカライド及びその誘導体の製造方法

オリゴサッカライド及びその誘導体の製造方法

Info

Publication number: JPS58170797A
Authority: JP; Japan
Prior art keywords: group; groups; unit; reaction; compound
Prior art date: 1982-01-15
Legal status : Granted

Application number

JP517883A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0565517B2 (enrdf_load_stackoverflow

Inventor

モ−リス・プチトウ

ジヤン−クロ−ド・ジヤキネ

ピエ−ル・シネ−

ジヤン・シヨアイ

ジヤン−クロ−ド・ロルモ

マ−ム−ド・ナ−スル

Current Assignee

Choay SA

Original Assignee

Choay SA

Priority date

1982-01-15

Filing date

1983-01-14

Publication date

1983-10-07

1983-01-14 Application filed by Choay SA filed Critical Choay SA

1983-10-07 Publication of JPS58170797A publication Critical patent/JPS58170797A/ja

1993-09-17 Publication of JPH0565517B2 publication Critical patent/JPH0565517B2/ja

Status Granted legal-status Critical Current

Links

229920001542 oligosaccharide Polymers 0.000 title claims description 59
150000002482 oligosaccharides Chemical class 0.000 title claims description 59
238000004519 manufacturing process Methods 0.000 title description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 158
239000000203 mixture Substances 0.000 claims description 133
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 123
150000001875 compounds Chemical class 0.000 claims description 110
238000006243 chemical reaction Methods 0.000 claims description 102
239000000047 product Substances 0.000 claims description 76
230000015572 biosynthetic process Effects 0.000 claims description 73
238000000034 method Methods 0.000 claims description 63
238000003786 synthesis reaction Methods 0.000 claims description 60
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 53
239000002253 acid Substances 0.000 claims description 41
239000002904 solvent Substances 0.000 claims description 37
239000004020 conductor Substances 0.000 claims description 35
150000004043 trisaccharides Chemical group 0.000 claims description 33
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 28
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 28
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 28
125000001424 substituent group Chemical group 0.000 claims description 28
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 27
239000000126 substance Substances 0.000 claims description 23
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 22
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 22
125000000524 functional group Chemical group 0.000 claims description 22
125000002252 acyl group Chemical group 0.000 claims description 20
239000011734 sodium Substances 0.000 claims description 20
-1 trichloroacetyl group Chemical group 0.000 claims description 20
125000000217 alkyl group Chemical group 0.000 claims description 19
239000003054 catalyst Substances 0.000 claims description 19
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
239000002609 medium Substances 0.000 claims description 19
230000008569 process Effects 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 18
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 17
239000002243 precursor Substances 0.000 claims description 17
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 16
230000007935 neutral effect Effects 0.000 claims description 16
229910052708 sodium Inorganic materials 0.000 claims description 16
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 15
238000005670 sulfation reaction Methods 0.000 claims description 15
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 14
125000006239 protecting group Chemical group 0.000 claims description 14
230000019635 sulfation Effects 0.000 claims 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 claims description 13
230000008859 change Effects 0.000 claims description 13
238000005755 formation reaction Methods 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
241001494479 Pecora Species 0.000 claims description 12
239000003153 chemical reaction reagent Substances 0.000 claims description 12
239000000543 intermediate Substances 0.000 claims description 12
229910052799 carbon Inorganic materials 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 11
150000002905 orthoesters Chemical class 0.000 claims description 11
125000000547 substituted alkyl group Chemical group 0.000 claims description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
239000012298 atmosphere Substances 0.000 claims description 10
150000001768 cations Chemical class 0.000 claims description 10
238000006206 glycosylation reaction Methods 0.000 claims description 10
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 10
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
150000002148 esters Chemical class 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
239000002585 base Substances 0.000 claims description 8
150000002016 disaccharides Chemical class 0.000 claims description 8
150000004820 halides Chemical class 0.000 claims description 8
229910052751 metal Inorganic materials 0.000 claims description 8
239000002184 metal Substances 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 8
229910052700 potassium Inorganic materials 0.000 claims description 8
238000007127 saponification reaction Methods 0.000 claims description 8
235000000346 sugar Nutrition 0.000 claims description 8
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 8
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 7
150000001412 amines Chemical class 0.000 claims description 7
125000003118 aryl group Chemical group 0.000 claims description 7
150000001720 carbohydrates Chemical class 0.000 claims description 7
239000003795 chemical substances by application Substances 0.000 claims description 7
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
229910052698 phosphorus Inorganic materials 0.000 claims description 7
239000011591 potassium Substances 0.000 claims description 7
239000007858 starting material Substances 0.000 claims description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 6
230000009471 action Effects 0.000 claims description 6
239000012634 fragment Substances 0.000 claims description 6
238000007306 functionalization reaction Methods 0.000 claims description 6
229930182470 glycoside Natural products 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
239000000463 material Substances 0.000 claims description 6
239000008194 pharmaceutical composition Substances 0.000 claims description 6
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
150000002338 glycosides Chemical class 0.000 claims description 5
230000007062 hydrolysis Effects 0.000 claims description 5
238000006460 hydrolysis reaction Methods 0.000 claims description 5
150000003138 primary alcohols Chemical class 0.000 claims description 5
230000009257 reactivity Effects 0.000 claims description 5
238000006467 substitution reaction Methods 0.000 claims description 5
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
125000003158 alcohol group Chemical group 0.000 claims description 4
150000001298 alcohols Chemical class 0.000 claims description 4
125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
230000000903 blocking effect Effects 0.000 claims description 4
150000001767 cationic compounds Chemical class 0.000 claims description 4
UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 claims description 4
150000002892 organic cations Chemical class 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
230000000717 retained effect Effects 0.000 claims description 4
239000010948 rhodium Substances 0.000 claims description 4
150000008163 sugars Chemical class 0.000 claims description 4
230000001180 sulfating effect Effects 0.000 claims description 4
ZXSQEZNORDWBGZ-UHFFFAOYSA-N 1,3-dihydropyrrolo[2,3-b]pyridin-2-one Chemical compound C1=CN=C2NC(=O)CC2=C1 ZXSQEZNORDWBGZ-UHFFFAOYSA-N 0.000 claims description 3
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
125000001931 aliphatic group Chemical group 0.000 claims description 3
125000003277 amino group Chemical group 0.000 claims description 3
150000001450 anions Chemical class 0.000 claims description 3
239000011575 calcium Substances 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
239000011777 magnesium Substances 0.000 claims description 3
NGYIMTKLQULBOO-UHFFFAOYSA-L mercury dibromide Chemical compound Br[Hg]Br NGYIMTKLQULBOO-UHFFFAOYSA-L 0.000 claims description 3
229910052703 rhodium Inorganic materials 0.000 claims description 3
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 3
LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 claims description 3
229910001958 silver carbonate Inorganic materials 0.000 claims description 3
ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 claims description 2
UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 claims description 2
RTKMFQOHBDVEBC-UHFFFAOYSA-N 3-bromo-3-buten-1-ol Chemical compound OCCC(Br)=C RTKMFQOHBDVEBC-UHFFFAOYSA-N 0.000 claims description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
229910052770 Uranium Inorganic materials 0.000 claims description 2
125000004036 acetal group Chemical group 0.000 claims description 2
230000002378 acidificating effect Effects 0.000 claims description 2
230000001476 alcoholic effect Effects 0.000 claims description 2
150000001449 anionic compounds Chemical class 0.000 claims description 2
IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
229910052791 calcium Inorganic materials 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
CZKMPDNXOGQMFW-UHFFFAOYSA-N chloro(triethyl)germane Chemical compound CC[Ge](Cl)(CC)CC CZKMPDNXOGQMFW-UHFFFAOYSA-N 0.000 claims description 2
MSWZFWKMSRAUBD-IVMDWMLBSA-N glucosamine group Chemical group OC1[C@H](N)[C@@H](O)[C@H](O)[C@H](O1)CO MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 claims description 2
230000013595 glycosylation Effects 0.000 claims description 2
239000011261 inert gas Substances 0.000 claims description 2
229910001412 inorganic anion Inorganic materials 0.000 claims description 2
229910001411 inorganic cation Inorganic materials 0.000 claims description 2
239000013067 intermediate product Substances 0.000 claims description 2
AEMOLEFTQBMNLQ-CLQWQSTFSA-N l-iduronic acid Chemical compound O[C@H]1O[C@H](C(O)=O)[C@H](O)[C@@H](O)[C@@H]1O AEMOLEFTQBMNLQ-CLQWQSTFSA-N 0.000 claims description 2
229910052744 lithium Inorganic materials 0.000 claims description 2
229910052749 magnesium Inorganic materials 0.000 claims description 2
229960002523 mercuric chloride Drugs 0.000 claims description 2
229940075610 mercuric cyanide Drugs 0.000 claims description 2
229940101209 mercuric oxide Drugs 0.000 claims description 2
LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 claims description 2
230000004048 modification Effects 0.000 claims description 2
238000012986 modification Methods 0.000 claims description 2
150000007530 organic bases Chemical class 0.000 claims description 2
239000011574 phosphorus Substances 0.000 claims description 2
150000003141 primary amines Chemical group 0.000 claims description 2
230000035484 reaction time Effects 0.000 claims description 2
230000004044 response Effects 0.000 claims description 2
150000003333 secondary alcohols Chemical class 0.000 claims description 2
238000006482 condensation reaction Methods 0.000 claims 4
150000002118 epoxides Chemical group 0.000 claims 3
GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims 2
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims 2
XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 claims 2
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims 2
239000002168 alkylating agent Substances 0.000 claims 2
229940100198 alkylating agent Drugs 0.000 claims 2
230000029936 alkylation Effects 0.000 claims 2
238000005804 alkylation reaction Methods 0.000 claims 2
150000001540 azides Chemical class 0.000 claims 2
238000009903 catalytic hydrogenation reaction Methods 0.000 claims 2
239000004744 fabric Substances 0.000 claims 2
230000002349 favourable effect Effects 0.000 claims 2
NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 claims 2
PCTMTFRHKVHKIS-BMFZQQSSSA-N (1s,3r,4e,6e,8e,10e,12e,14e,16e,18s,19r,20r,21s,25r,27r,30r,31r,33s,35r,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10 Chemical compound C1C=C2C[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2.O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 PCTMTFRHKVHKIS-BMFZQQSSSA-N 0.000 claims 1
229930024421 Adenine Natural products 0.000 claims 1
241000345998 Calamus manan Species 0.000 claims 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
102100040996 Cochlin Human genes 0.000 claims 1
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 1
101000748988 Homo sapiens Cochlin Proteins 0.000 claims 1
108091034117 Oligonucleotide Proteins 0.000 claims 1
JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 claims 1
239000012345 acetylating agent Substances 0.000 claims 1
229960000643 adenine Drugs 0.000 claims 1
229910052783 alkali metal Inorganic materials 0.000 claims 1
150000001340 alkali metals Chemical class 0.000 claims 1
239000012736 aqueous medium Substances 0.000 claims 1
125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims 1
150000001649 bromium compounds Chemical class 0.000 claims 1
150000001805 chlorine compounds Chemical class 0.000 claims 1
230000032050 esterification Effects 0.000 claims 1
238000005886 esterification reaction Methods 0.000 claims 1
150000008134 glucuronides Chemical group 0.000 claims 1
150000002463 imidates Chemical class 0.000 claims 1
229910052500 inorganic mineral Inorganic materials 0.000 claims 1
238000012423 maintenance Methods 0.000 claims 1
150000002730 mercury Chemical class 0.000 claims 1
239000011707 mineral Substances 0.000 claims 1
229930014626 natural product Natural products 0.000 claims 1
125000002524 organometallic group Chemical group 0.000 claims 1
238000004806 packaging method and process Methods 0.000 claims 1
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
150000003014 phosphoric acid esters Chemical class 0.000 claims 1
229960005235 piperonyl butoxide Drugs 0.000 claims 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 claims 1
235000012950 rattan cane Nutrition 0.000 claims 1
229910052710 silicon Inorganic materials 0.000 claims 1
239000010703 silicon Substances 0.000 claims 1
229910001923 silver oxide Inorganic materials 0.000 claims 1
229910021653 sulphate ion Inorganic materials 0.000 claims 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 243
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 215
239000000243 solution Substances 0.000 description 148
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 140
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