JP2003519628A5 - - Google Patents
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- Publication number
- JP2003519628A5 JP2003519628A5 JP2001551083A JP2001551083A JP2003519628A5 JP 2003519628 A5 JP2003519628 A5 JP 2003519628A5 JP 2001551083 A JP2001551083 A JP 2001551083A JP 2001551083 A JP2001551083 A JP 2001551083A JP 2003519628 A5 JP2003519628 A5 JP 2003519628A5
- Authority
- JP
- Japan
- Prior art keywords
- galactopyranoside
- benzylidene
- galactopyranosyl
- ethoxy
- solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 25
- 239000000243 solution Substances 0.000 description 23
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000011347 resin Substances 0.000 description 12
- 229920005989 resin Polymers 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 10
- 235000019439 ethyl acetate Nutrition 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- -1 dimethyl (methylthio) sulfonium tetrafluoroborate Chemical compound 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 229920006395 saturated elastomer Polymers 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- ZFUXASUEDJQOIH-RRDFSISJSA-N CCO[C@@H]([C@@H]([C@H]1O[C@H]([C@@H]([C@H]2O)O)O[C@H](CO)[C@@H]2O)OC(C(C=C2)=CC=C2Cl)=O)O[C@H](CO)[C@@H]1O Chemical compound CCO[C@@H]([C@@H]([C@H]1O[C@H]([C@@H]([C@H]2O)O)O[C@H](CO)[C@@H]2O)OC(C(C=C2)=CC=C2Cl)=O)O[C@H](CO)[C@@H]1O ZFUXASUEDJQOIH-RRDFSISJSA-N 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 239000012266 salt solution Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- COTSIKNPSXUELW-WVYBCTLKSA-N (2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5s,6r)-2-ethoxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@H]1[C@H](OCC)O[C@H](CO)[C@H](O)[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 COTSIKNPSXUELW-WVYBCTLKSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- DITDTNOZNUKKDC-NXRLNHOXSA-N [(2s,3r,4s,5r,6r)-4,5-dihydroxy-6-(hydroxymethyl)-2-methylsulfanyloxan-3-yl] acetate Chemical compound CS[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1OC(C)=O DITDTNOZNUKKDC-NXRLNHOXSA-N 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000002808 molecular sieve Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- OIRDBPQYVWXNSJ-UHFFFAOYSA-N methyl trifluoromethansulfonate Chemical compound COS(=O)(=O)C(F)(F)F OIRDBPQYVWXNSJ-UHFFFAOYSA-N 0.000 description 3
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 2
- KECMLGZOQMJIBM-UHFFFAOYSA-N 2-[2-(2-chloroethoxy)ethoxy]ethanol Chemical compound OCCOCCOCCCl KECMLGZOQMJIBM-UHFFFAOYSA-N 0.000 description 2
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CRVZIAHSTWXQJC-NVCPMKERSA-N (2r,3s,4s,5r,6s)-3,4,5-tris[(4-chlorophenyl)methoxy]-2-[(4-chlorophenyl)methoxymethyl]-6-methylsulfanyloxane Chemical compound C([C@H]1O[C@H]([C@@H]([C@@H](OCC=2C=CC(Cl)=CC=2)[C@H]1OCC=1C=CC(Cl)=CC=1)OCC=1C=CC(Cl)=CC=1)SC)OCC1=CC=C(Cl)C=C1 CRVZIAHSTWXQJC-NVCPMKERSA-N 0.000 description 1
- HEVMDQBCAHEHDY-UHFFFAOYSA-N (Dimethoxymethyl)benzene Chemical compound COC(OC)C1=CC=CC=C1 HEVMDQBCAHEHDY-UHFFFAOYSA-N 0.000 description 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
- MPJOJCZVGBOVOV-UHFFFAOYSA-N 2-phenylbenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1C1=CC=CC=C1 MPJOJCZVGBOVOV-UHFFFAOYSA-N 0.000 description 1
- QJNLUNBGDFUULX-UHFFFAOYSA-N 4-n,4-n'-dimethyl-3h-pyridine-4,4-diamine Chemical compound CNC1(NC)CC=NC=C1 QJNLUNBGDFUULX-UHFFFAOYSA-N 0.000 description 1
- AUALQMFGWLZREY-UHFFFAOYSA-N acetonitrile;methanol Chemical compound OC.CC#N AUALQMFGWLZREY-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- QRPYHTZAJOUHAQ-UHFFFAOYSA-M cesium;thiobenzate Chemical compound [Cs+].[O-]C(=S)C1=CC=CC=C1 QRPYHTZAJOUHAQ-UHFFFAOYSA-M 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
- IRXSLJNXXZKURP-UHFFFAOYSA-N fluorenylmethyloxycarbonyl chloride Chemical compound C1=CC=C2C(COC(=O)Cl)C3=CC=CC=C3C2=C1 IRXSLJNXXZKURP-UHFFFAOYSA-N 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- RYVMUASDIZQXAA-UHFFFAOYSA-N pyranoside Natural products O1C2(OCC(C)C(OC3C(C(O)C(O)C(CO)O3)O)C2)C(C)C(C2(CCC3C4(C)CC5O)C)C1CC2C3CC=C4CC5OC(C(C1O)O)OC(CO)C1OC(C1OC2C(C(OC3C(C(O)C(O)C(CO)O3)O)C(O)C(CO)O2)O)OC(CO)C(O)C1OC1OCC(O)C(O)C1O RYVMUASDIZQXAA-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000008259 solid foam Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AUPQ5073A AUPQ507300A0 (en) | 2000-01-13 | 2000-01-13 | Methods for synthesis of alpha-d-gal(1-3) gal containing oligosaccharides |
| AU5073 | 2000-01-13 | ||
| AU9734 | 2000-08-29 | ||
| AUPQ9734A AUPQ973400A0 (en) | 2000-08-29 | 2000-08-29 | Methods for synthesis of alpha-d-gal(1-3) gal containing oligosaccharides |
| PCT/AU2001/000028 WO2001051499A1 (en) | 2000-01-13 | 2001-01-12 | METHODS FOR SYNTHESIS OF α-D-GAL (1→3) GAL-CONTAINING OLIGOSACCHARIDES |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003519628A JP2003519628A (ja) | 2003-06-24 |
| JP2003519628A5 true JP2003519628A5 (https=) | 2005-05-19 |
Family
ID=25646242
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001551083A Pending JP2003519628A (ja) | 2000-01-13 | 2001-01-12 | α−Ｄ−ＧＡＬ（１→３）ＧＡＬ−含有オリゴ糖の合成方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20040058888A1 (https=) |
| EP (1) | EP1257558A1 (https=) |
| JP (1) | JP2003519628A (https=) |
| CN (1) | CN1395579A (https=) |
| CA (1) | CA2396966A1 (https=) |
| HU (1) | HUP0204225A2 (https=) |
| IL (1) | IL150410A0 (https=) |
| WO (1) | WO2001051499A1 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AUPR079700A0 (en) | 2000-10-17 | 2000-11-09 | Alchemia Pty Ltd | Combinatorial libraries of monosaccharides |
| AUPS213802A0 (en) * | 2002-05-03 | 2002-06-06 | Alchemia Pty Ltd | Disaccharides for drug discovery |
| AU2002952121A0 (en) | 2002-10-17 | 2002-10-31 | Alchemia Limited | Novel carbohydrate based anti-bacterials |
| WO2009052148A1 (en) * | 2007-10-15 | 2009-04-23 | California Institute Of Technology | Functionalized polymers using protected thiols |
| CN102977159A (zh) * | 2012-11-18 | 2013-03-20 | 大连九信生物化工科技有限公司 | 一种苄醚保护d-氨基葡萄糖衍生物c3位上羟基的制备方法 |
| EP2987503A1 (en) * | 2014-08-22 | 2016-02-24 | Institut d'Investigació Biomèdica de Bellvitge (IDIBELL) | Methods and reagents for prevention and/or treatment of infection |
| NL2023572B1 (en) * | 2019-07-25 | 2021-02-10 | Synaffix Bv | Synthesis of 6-azido-6-deoxy-2-N-acetyl-hexosamine-nucleoside diphosphate |
| CN113416220B (zh) * | 2021-06-24 | 2023-07-18 | 宁波职业技术学院 | 一种硫代葡萄糖类化合物及其制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU666128B2 (en) * | 1991-08-23 | 1996-02-01 | Alberta Research Council Inc. | Methods and compositions for attenuating antibody-mediated xenograft rejection in human recipients |
| ES2249890T3 (es) * | 1998-04-15 | 2006-04-01 | Mayo Foundation For Medical Education And Research | Inhibicion de anticuerpos xenorreactivos. |
-
2001
- 2001-01-12 EP EP01901031A patent/EP1257558A1/en not_active Withdrawn
- 2001-01-12 WO PCT/AU2001/000028 patent/WO2001051499A1/en not_active Ceased
- 2001-01-12 HU HU0204225A patent/HUP0204225A2/hu unknown
- 2001-01-12 US US10/181,027 patent/US20040058888A1/en not_active Abandoned
- 2001-01-12 CN CN01803721A patent/CN1395579A/zh active Pending
- 2001-01-12 CA CA002396966A patent/CA2396966A1/en not_active Abandoned
- 2001-01-12 IL IL15041001A patent/IL150410A0/xx unknown
- 2001-01-12 JP JP2001551083A patent/JP2003519628A/ja active Pending
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