CN103665063A - 一种制备异丙基-β-D-硫代半乳糖苷的方法 - Google Patents
一种制备异丙基-β-D-硫代半乳糖苷的方法 Download PDFInfo
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- CN103665063A CN103665063A CN201310671229.3A CN201310671229A CN103665063A CN 103665063 A CN103665063 A CN 103665063A CN 201310671229 A CN201310671229 A CN 201310671229A CN 103665063 A CN103665063 A CN 103665063A
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- isopropyl
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- 238000000034 method Methods 0.000 title claims abstract description 34
- BPHPUYQFMNQIOC-NXRLNHOXSA-N isopropyl beta-D-thiogalactopyranoside Chemical compound CC(C)S[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O BPHPUYQFMNQIOC-NXRLNHOXSA-N 0.000 claims abstract description 39
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims abstract description 33
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 24
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims abstract description 22
- KJRCEJOSASVSRA-UHFFFAOYSA-N propane-2-thiol Chemical compound CC(C)S KJRCEJOSASVSRA-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- -1 isopropylthio acetyl Chemical group 0.000 claims description 16
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 13
- 238000002425 crystallisation Methods 0.000 claims description 13
- 230000008025 crystallization Effects 0.000 claims description 13
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical group Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 10
- 239000012046 mixed solvent Substances 0.000 claims description 8
- 238000000605 extraction Methods 0.000 claims description 7
- 238000006386 neutralization reaction Methods 0.000 claims description 7
- 238000005406 washing Methods 0.000 claims description 7
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 4
- 239000011877 solvent mixture Substances 0.000 claims description 4
- 235000005074 zinc chloride Nutrition 0.000 claims description 3
- 239000011592 zinc chloride Substances 0.000 claims description 3
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 2
- 239000002994 raw material Substances 0.000 abstract description 5
- 239000003054 catalyst Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 238000007039 two-step reaction Methods 0.000 abstract description 2
- 229930182830 galactose Natural products 0.000 abstract 1
- 230000003472 neutralizing effect Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 17
- 239000012074 organic phase Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 5
- 239000011259 mixed solution Substances 0.000 description 5
- 230000008569 process Effects 0.000 description 3
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 229960004249 sodium acetate Drugs 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (10)
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CN201310671229.3A CN103665063B (zh) | 2013-12-12 | 2013-12-12 | 一种制备异丙基-β-D-硫代半乳糖苷的方法 |
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CN201310671229.3A CN103665063B (zh) | 2013-12-12 | 2013-12-12 | 一种制备异丙基-β-D-硫代半乳糖苷的方法 |
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CN103665063A true CN103665063A (zh) | 2014-03-26 |
CN103665063B CN103665063B (zh) | 2016-04-27 |
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CN201310671229.3A Active CN103665063B (zh) | 2013-12-12 | 2013-12-12 | 一种制备异丙基-β-D-硫代半乳糖苷的方法 |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103880897A (zh) * | 2014-04-04 | 2014-06-25 | 济南圣泉唐和唐生物科技有限公司 | 一种对甲苯基-β-D-硫代乙酰半乳糖苷的制备方法 |
CN105566410A (zh) * | 2016-02-26 | 2016-05-11 | 宁波欧曼生物科技有限公司 | 一种异丙基-β-D-硫代吡喃半乳糖苷的制备方法 |
CN110143987A (zh) * | 2019-05-30 | 2019-08-20 | 山东大学 | 一种异丙基-β-硫代半乳糖苷的纯化方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4675393A (en) * | 1982-04-02 | 1987-06-23 | Lever Brothers Company | Process for preparing glucose penta-acetate and xylose tetra-acetate |
CN102993246A (zh) * | 2012-12-19 | 2013-03-27 | 北京利德曼生化股份有限公司 | 一种合成异丙基-β-D-硫代半乳糖苷的方法 |
CN103087121A (zh) * | 2013-01-12 | 2013-05-08 | 江西师范大学 | 异丙基-β-D硫代半乳糖苷的合成方法 |
-
2013
- 2013-12-12 CN CN201310671229.3A patent/CN103665063B/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4675393A (en) * | 1982-04-02 | 1987-06-23 | Lever Brothers Company | Process for preparing glucose penta-acetate and xylose tetra-acetate |
CN102993246A (zh) * | 2012-12-19 | 2013-03-27 | 北京利德曼生化股份有限公司 | 一种合成异丙基-β-D-硫代半乳糖苷的方法 |
CN103087121A (zh) * | 2013-01-12 | 2013-05-08 | 江西师范大学 | 异丙基-β-D硫代半乳糖苷的合成方法 |
Non-Patent Citations (1)
Title |
---|
田晓红: "乳糖基胍及硫代糖苷的合成", 《新疆大学硕士研究生学位论文》, 2 June 2007 (2007-06-02) * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103880897A (zh) * | 2014-04-04 | 2014-06-25 | 济南圣泉唐和唐生物科技有限公司 | 一种对甲苯基-β-D-硫代乙酰半乳糖苷的制备方法 |
CN105566410A (zh) * | 2016-02-26 | 2016-05-11 | 宁波欧曼生物科技有限公司 | 一种异丙基-β-D-硫代吡喃半乳糖苷的制备方法 |
CN110143987A (zh) * | 2019-05-30 | 2019-08-20 | 山东大学 | 一种异丙基-β-硫代半乳糖苷的纯化方法 |
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