CN103665057A - 一种溴代四乙酰葡萄糖的合成方法 - Google Patents
一种溴代四乙酰葡萄糖的合成方法 Download PDFInfo
- Publication number
- CN103665057A CN103665057A CN201310625687.3A CN201310625687A CN103665057A CN 103665057 A CN103665057 A CN 103665057A CN 201310625687 A CN201310625687 A CN 201310625687A CN 103665057 A CN103665057 A CN 103665057A
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- Prior art keywords
- bromotetraacetylgluc
- glucose
- water
- acetyl glucose
- reaction
- 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.)
- Granted
Links
- 238000010189 synthetic method Methods 0.000 title claims abstract description 8
- FRSGBCDEXJLPAE-HRFRYAEBSA-N (18R,19R,20S)-20-[(1S)-1-bromo-1,2-dihydroxyethyl]-18,19-dihexadecyl-18,19,20-trihydroxyhexatriacontan-17-one Chemical compound Br[C@@]([C@]([C@@]([C@](C(=O)CCCCCCCCCCCCCCCC)(O)CCCCCCCCCCCCCCCC)(O)CCCCCCCCCCCCCCCC)(O)CCCCCCCCCCCCCCCC)(O)CO FRSGBCDEXJLPAE-HRFRYAEBSA-N 0.000 title abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 16
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 24
- HXBYBCASAVUYKF-GVYWOMJSSA-N (4r,5s,6r,7r)-4,5,6,7,8-pentahydroxyoctane-2,3-dione Chemical compound CC(=O)C(=O)[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO HXBYBCASAVUYKF-GVYWOMJSSA-N 0.000 claims description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 14
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 10
- 229960001031 glucose Drugs 0.000 claims description 10
- 239000008103 glucose Substances 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 9
- 239000000047 product Substances 0.000 claims description 8
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 6
- 239000012074 organic phase Substances 0.000 claims description 6
- SPFMQWBKVUQXJV-BTVCFUMJSA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal;hydrate Chemical compound O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O SPFMQWBKVUQXJV-BTVCFUMJSA-N 0.000 claims description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 5
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 5
- 229960000673 dextrose monohydrate Drugs 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 5
- 239000005457 ice water Substances 0.000 claims description 5
- 230000002194 synthesizing effect Effects 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 3
- MNZMECMQTYGSOI-UHFFFAOYSA-N acetic acid;hydron;bromide Chemical compound Br.CC(O)=O MNZMECMQTYGSOI-UHFFFAOYSA-N 0.000 claims description 3
- 239000012065 filter cake Substances 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 229930182478 glucoside Natural products 0.000 claims description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 2
- YDVNLQGCLLPHAH-UHFFFAOYSA-N dichloromethane;hydrate Chemical compound O.ClCCl YDVNLQGCLLPHAH-UHFFFAOYSA-N 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims description 2
- 239000000706 filtrate Substances 0.000 claims description 2
- 150000008131 glucosides Chemical class 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 235000002639 sodium chloride Nutrition 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract description 12
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 5
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 abstract 1
- 230000021736 acetylation Effects 0.000 abstract 1
- 238000006640 acetylation reaction Methods 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000011031 large-scale manufacturing process Methods 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 11
- 125000001246 bromo group Chemical group Br* 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001273 acylsugars Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- -1 supply with energy Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- PUQSUZTXKPLAPR-KSSYENDESA-N 4-(beta-D-Glucopyranosyloxy) benzyl alcohol Natural products O([C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1)c1ccc(CO)cc1 PUQSUZTXKPLAPR-KSSYENDESA-N 0.000 description 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- PUQSUZTXKPLAPR-UJPOAAIJSA-N Gastrodin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=C(CO)C=C1 PUQSUZTXKPLAPR-UJPOAAIJSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- LPQOADBMXVRBNX-UHFFFAOYSA-N ac1ldcw0 Chemical compound Cl.C1CN(C)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN3CCSC1=C32 LPQOADBMXVRBNX-UHFFFAOYSA-N 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 229930193974 gastrodin Natural products 0.000 description 2
- 229930182470 glycoside Natural products 0.000 description 2
- PUQSUZTXKPLAPR-NZEXEKPDSA-N helicidol Natural products O([C@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](CO)O1)c1ccc(CO)cc1 PUQSUZTXKPLAPR-NZEXEKPDSA-N 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 150000001262 acyl bromides Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 210000001124 body fluid Anatomy 0.000 description 1
- 239000010839 body fluid Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000000496 cardiotonic agent Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 230000035619 diuresis Effects 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 230000036267 drug metabolism Effects 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 150000002303 glucose derivatives Chemical class 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 125000003147 glycosyl group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000000050 nutritive effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000021715 photosynthesis, light harvesting Effects 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
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Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106397504A (zh) * | 2016-08-31 | 2017-02-15 | 重庆欣欣向荣精细化工有限公司 | 一种五乙酰葡萄糖的生产方法 |
CN108997454A (zh) * | 2018-09-05 | 2018-12-14 | 青岛农业大学 | 一种β-熊果苷的化学合成方法 |
CN111100102A (zh) * | 2019-11-22 | 2020-05-05 | 吉尔生化(上海)有限公司 | 一种3,4,6-o-三乙酰基-d-葡萄糖烯的制备方法 |
CN112159441A (zh) * | 2020-10-15 | 2021-01-01 | 北京悦康科创医药科技股份有限公司 | 一种天麻素中间体的合成方法及应用 |
CN112608355A (zh) * | 2020-12-17 | 2021-04-06 | 北京悦康科创医药科技股份有限公司 | 一种四乙酰葡萄糖的制备方法 |
CN114591280A (zh) * | 2020-12-04 | 2022-06-07 | 南京圣鼎医药科技有限公司 | 一种α-溴代葡萄糖的制备方法 |
CN114591385A (zh) * | 2020-12-04 | 2022-06-07 | 南京圣鼎医药科技有限公司 | 一种α-溴代葡萄糖及其制备方法 |
Citations (2)
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CN101857616A (zh) * | 2010-06-09 | 2010-10-13 | 南京工业大学 | 葛根素葡萄糖衍生物的一种制备方法 |
CN102516329A (zh) * | 2011-11-25 | 2012-06-27 | 上海现代哈森(商丘)药业有限公司 | 天麻素合成方法 |
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2013
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Patent Citations (2)
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CN101857616A (zh) * | 2010-06-09 | 2010-10-13 | 南京工业大学 | 葛根素葡萄糖衍生物的一种制备方法 |
CN102516329A (zh) * | 2011-11-25 | 2012-06-27 | 上海现代哈森(商丘)药业有限公司 | 天麻素合成方法 |
Non-Patent Citations (2)
Title |
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PAUL FREE,ET AL: ""Mannose–pepstatin conjugates as targeted inhibitors of antigen processing"", 《ORGANIC & BIOMOLECULAR CHEMISTRY》, no. 4, 4 April 2006 (2006-04-04), pages 1817 - 1830 * |
刘媛媛,等,: ""五乙酰葡萄糖的合成工艺研究"", 《科技视界》, no. 29, 15 October 2012 (2012-10-15), pages 422 - 423 * |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106397504A (zh) * | 2016-08-31 | 2017-02-15 | 重庆欣欣向荣精细化工有限公司 | 一种五乙酰葡萄糖的生产方法 |
CN108997454A (zh) * | 2018-09-05 | 2018-12-14 | 青岛农业大学 | 一种β-熊果苷的化学合成方法 |
CN108997454B (zh) * | 2018-09-05 | 2023-03-21 | 青岛农业大学 | 一种β-熊果苷的化学合成方法 |
CN111100102A (zh) * | 2019-11-22 | 2020-05-05 | 吉尔生化(上海)有限公司 | 一种3,4,6-o-三乙酰基-d-葡萄糖烯的制备方法 |
CN112159441A (zh) * | 2020-10-15 | 2021-01-01 | 北京悦康科创医药科技股份有限公司 | 一种天麻素中间体的合成方法及应用 |
CN114591280A (zh) * | 2020-12-04 | 2022-06-07 | 南京圣鼎医药科技有限公司 | 一种α-溴代葡萄糖的制备方法 |
CN114591385A (zh) * | 2020-12-04 | 2022-06-07 | 南京圣鼎医药科技有限公司 | 一种α-溴代葡萄糖及其制备方法 |
CN112608355A (zh) * | 2020-12-17 | 2021-04-06 | 北京悦康科创医药科技股份有限公司 | 一种四乙酰葡萄糖的制备方法 |
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Inventor after: Chen Honghui Inventor before: You Xiaoming Inventor before: Li Yang Inventor before: Liu Guohua Inventor before: Zhang Lanpeng Inventor before: Ge Ruhai Inventor before: Yan Jixiang |
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Denomination of invention: A synthetic method of bromotetraacetylglucose Effective date of registration: 20210525 Granted publication date: 20160413 Pledgee: Jinhua Branch of Bank of Ningbo Co.,Ltd. Pledgor: SYNGARS TECHNOLOGY Co.,Ltd. Registration number: Y2021330000449 |
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