CN108484667A - 一种新化合物磷酯酰3-羟基丙腈的合成工艺 - Google Patents
一种新化合物磷酯酰3-羟基丙腈的合成工艺 Download PDFInfo
- Publication number
- CN108484667A CN108484667A CN201810236466.XA CN201810236466A CN108484667A CN 108484667 A CN108484667 A CN 108484667A CN 201810236466 A CN201810236466 A CN 201810236466A CN 108484667 A CN108484667 A CN 108484667A
- Authority
- CN
- China
- Prior art keywords
- phosphatidyl
- raw material
- hydroxypropionitriles
- compound
- chemical compound
- 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
- 238000005516 engineering process Methods 0.000 title claims abstract description 18
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 17
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 14
- -1 phosphine oxide compound Chemical class 0.000 claims abstract description 20
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims abstract description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
- RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical compound CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000001095 phosphatidyl group Chemical group 0.000 claims abstract description 7
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 6
- 239000007858 starting material Substances 0.000 claims abstract description 6
- 235000021355 Stearic acid Nutrition 0.000 claims abstract description 5
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims abstract description 5
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000008117 stearic acid Substances 0.000 claims abstract description 5
- 238000005660 chlorination reaction Methods 0.000 claims abstract description 4
- 230000032050 esterification Effects 0.000 claims abstract description 4
- 238000005886 esterification reaction Methods 0.000 claims abstract description 4
- 230000003647 oxidation Effects 0.000 claims abstract description 4
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 4
- 239000002994 raw material Substances 0.000 claims description 18
- 239000000126 substance Substances 0.000 claims description 10
- 238000000746 purification Methods 0.000 claims description 5
- 230000026030 halogenation Effects 0.000 claims description 4
- 238000005658 halogenation reaction Methods 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 238000001953 recrystallisation Methods 0.000 claims description 3
- 230000031709 bromination Effects 0.000 claims description 2
- 238000005893 bromination reaction Methods 0.000 claims description 2
- 238000004440 column chromatography Methods 0.000 claims description 2
- 150000002170 ethers Chemical group 0.000 claims description 2
- 239000012467 final product Substances 0.000 claims description 2
- 125000006289 hydroxybenzyl group Chemical group 0.000 claims description 2
- QAXHWUAAPKHMGA-UHFFFAOYSA-N iodophosphane Chemical compound IP QAXHWUAAPKHMGA-UHFFFAOYSA-N 0.000 claims description 2
- 125000003473 lipid group Chemical group 0.000 claims 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 abstract description 2
- WSGYTJNNHPZFKR-UHFFFAOYSA-N 3-hydroxypropanenitrile Chemical compound OCCC#N WSGYTJNNHPZFKR-UHFFFAOYSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 229910052698 phosphorus Inorganic materials 0.000 description 7
- 239000011574 phosphorus Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000007445 Chromatographic isolation Methods 0.000 description 6
- 238000011097 chromatography purification Methods 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 125000006355 carbonyl methylene group Chemical group [H]C([H])([*:2])C([*:1])=O 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- WOFDVDFSGLBFAC-UHFFFAOYSA-N lactonitrile Chemical compound CC(O)C#N WOFDVDFSGLBFAC-UHFFFAOYSA-N 0.000 description 1
- 150000002632 lipids Chemical group 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- YHHSONZFOIEMCP-UHFFFAOYSA-O phosphocholine Chemical compound C[N+](C)(C)CCOP(O)(O)=O YHHSONZFOIEMCP-UHFFFAOYSA-O 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4075—Esters with hydroxyalkyl compounds
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Abstract
本发明涉及新化合物磷酯酰3‑羟基丙腈的合成工艺。采用丙酮缩甘油为起始物料，苄基保护裸露羟基，脱去缩酮保护基得到二个裸露羟基，再与硬脂酸发生酯化反应，脱去苄基保护得到裸露羟基，再与氯化膦类化合物得到膦氧化合物，氧化得到氧化膦，脱去一分子丙基腈得到最终产品磷酯酰3‑羟基丙腈。
Description
技术领域
本发明涉及磷酯类化合物的合成工艺，更具体地说，涉及一种新化合物磷酯酰3-羟基丙腈的合成工艺。
背景技术
磷脂类化合物是一类广泛存在于自然界中的化合物，磷酯类化合物商品化生产也有近百年的历史。膳食中磷酸胆碱为人们提供必须脂肪酸和胆碱，磷酸酰甘油可以调节血清脂质，磷酸酰丝氨酸对大脑老化调节。磷酯类化合物除上述价值外,还由于它的多种功能特性如乳化、防溅、速溶、润湿、分散、脱模、分离、改善粘度及营养源等,使得磷脂产品理想地用于食品领域。并由于作为一种天然产物,受到消费者普遍接受,我国的多种保健饮品也都标明强化了磷脂。
目前关于磷脂类化合物的制备方法主要是提取法，包括物理萃取法：超临界流体技术；化学萃取法：即用氯仿、甲醇、乙醇、丙酮、乙醚等有机溶剂反复萃取，其操作步骤比较复杂。但是磷酯类化合物的化学合成报道较少，因此此合成方法提供了一种磷酯类化合物的全新合成方法，为更深人的磷酯类化合物的研究提供了制备手段，具有广泛的应用前景。
发明内容
本发明要解决的技术问题在于，针对新化合物磷酯酰3-羟基丙腈的合成工艺，提供一种以丙酮缩甘油为起始物料，通过一系列化学反应得到新化合物磷酯酰3-羟基丙腈的合成工艺。
本发明解决其技术问题所采用的技术方案是：构造一种新化合物磷酯酰3-羟基丙腈的合成工艺，合成路线如下：
包括以下步骤：
S1以丙酮缩甘油为起始原料，加入保护基，对所述丙酮缩甘油的羟基苄基保护，从而生成中间体1；
S2以所述步骤S1中的中间体1为原料，脱去缩酮保护基得到两个裸露羟基，从而生成中间体2；
S3以所述步骤S2中的中间体2为原料，与硬脂酸发生酯化反应，从而生成中间体3；
S4以所述步骤S3中的中间体3为原料，脱去苄基保护得到裸露羟基，从而生成中间体4；
S5以所述步骤S4中的中间体4为原料，与卤化膦类化合物反应，从而生成中间体5；
S6以所述步骤S5中的中间体5为原料，氧化，从而生成中间体6；
S7以所述步骤S6中的中间体6为原料，脱去一分子丙基腈，得到最终产物磷酯酰3-羟基丙腈；
本发明所述的一种新化合物磷酯酰3-羟基丙腈的合成工艺，其特征在于，所述步骤S1中的保护基，进一步地为脂类保护基，醚类保护基。
本发明所述的一种新化合物磷酯酰3-羟基丙腈的合成工艺，其特征在于，所述步骤S5中的卤化膦类化合物，进一步地为氯化膦类化合物、溴化膦类化合物、碘代膦类化合物。
本发明所述的一种新化合物磷酯酰3-羟基丙腈的合成工艺，其特征在于，所述步骤S1至S7中任一步骤，都要经过纯化处理，所述纯化处理为层析柱纯化、重结晶。
采用丙酮缩甘油为起始物料，苄基保护裸露羟基，脱去缩酮保护基得到二个裸露羟基，再与硬脂酸发生酯化反应，脱去苄基保护得到裸露羟基，再与氯化膦类化合物得到膦氧化合物，氧化得到氧化膦，脱去一分子丙基腈得到最终产品磷酯酰3-羟基丙腈，其每一步反应都要经过纯化处理，纯度达到98%以上，并且产率高。此磷酯酰3-羟基丙腈为新化合物，同时为磷脂类化合物提供了化学合成方法。
附图说明：图1是本发明获得的磷酯酰3-羟基丙腈的核磁氢谱图；
以下通过实施例形式再对本发明的内容做进一步详细说明，但不应就此理解为本发明上述主题范围内仅限于以下实施例。在不脱离本发明上述技术前提下，根据本领域普通技术知识和惯用手段做出的相应替换或变更的修改，均包括在本发明内。
实施例1
以丙酮缩甘油为起始原料，溶于四氢呋喃中，依次加入氢化钠、四丁基碘化铵、苄溴，室温条件下，反应10小时，TLC检测反应进度，淬灭反应，过滤，浓缩，产品乙醇重结晶纯化得到中间体1，这一步的化学反应式为：
以中间体1为原料，溶于四氢呋喃水溶液中（1:1），滴加2N HCl水溶液反应半小时，加热回流反应8小时TLC检测反应进度，加碱液，乙酸乙酯萃取，水洗涤，浓缩，柱层析分离纯化得到中间体2，这一步的化学反应式为：
以中间体2为原料，溶于三氯甲烷中，依次加入硬脂酸、浓硫酸，加热回流反应8小时，淬灭反应，用水洗涤，浓缩，柱层析分离纯化得到中间体3，这一步的化学反应式为：
以中间体3为原料，溶于甲醇中，加入氢氧化钯碳，并通入氢气反应16小时，淬灭反应，用水洗涤，浓缩，柱层析分离纯化得到中间体4，这一步的化学反应式为：
以中间体4为原料，溶于THF中，依次加入DMAP，二（丙基腈）氯化磷，加热回流反应8小时，淬灭反应，用水洗涤，浓缩，柱层析分离纯化得到中间体5，这一步的化学反应式为：
以中间体5为原料，溶于THF中，加入双氧水，室温反应2小时，淬灭反应，用水洗涤，浓缩，柱层析分离纯化得到中间体6，这一步的化学反应式为：
以中间体6为原料，溶于甲醇中，加入PCC，加热回流反应12小时，淬灭反应，用水洗涤，浓缩，柱层析分离纯化得到终产品磷酯酰3-羟基丙腈，纯度98%以上，这一步的化学反应式为：
1HNMR (400 MHz,CDCl3): δ = 0.89 (d, 7H, CH3, CH2), 1.27 (m, 55H, CH2),2.09 (m, 4H, CH2), 2.31-2.33 (dd, 5H, COCH2), 2.80 (dd,2H, CNCH2), 4.11-4.13(dd, 7H, CH2, CH)，谱图见图1。
Claims (4)
1.一种新化合物磷酯酰3-羟基丙腈的合成工艺，其特征在于，包括以下步骤：
S1以丙酮缩甘油为起始原料，加入保护基，对所述丙酮缩甘油的羟基苄基保护，从而生成中间体1；
S2以所述步骤S1中的中间体1为原料，脱去缩酮保护基得到两个裸露羟基，从而生成中间体2；
S3以所述步骤S2中的中间体2为原料，与硬脂酸发生酯化反应，从而生成中间体3；
S4以所述步骤S3中的中间体3为原料，脱去苄基保护得到裸露羟基，从而生成中间体4；
S5以所述步骤S4中的中间体4为原料，与卤化膦类化合物反应，从而生成中间体5；
S6以所述步骤S5中的中间体5为原料，氧化，从而生成中间体6；
S7以所述步骤S6中的中间体6为原料，脱去一分子丙基腈，得到最终产物磷酯酰3-羟基丙腈。
2.如权利要求1所述的一种新化合物磷酯酰3-羟基丙腈的合成工艺，其特征在于，所述步骤S1中的保护基，进一步地为脂类保护基，醚类保护基。
3.如权利要求1所述的一种新化合物磷酯酰3-羟基丙腈的合成工艺，其特征在于，所述步骤S5中的卤化膦类化合物，进一步地为氯化膦类化合物、溴化膦类化合物、碘代膦类化合物。
4.如权利要求1所述的一种新化合物磷酯酰3-羟基丙腈的合成工艺，其特征在于，所述步骤S1至S7中任一步骤，都要经过纯化处理，所述纯化处理为层析柱纯化、重结晶。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810236466.XA CN108484667A (zh) | 2018-03-21 | 2018-03-21 | 一种新化合物磷酯酰3-羟基丙腈的合成工艺 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810236466.XA CN108484667A (zh) | 2018-03-21 | 2018-03-21 | 一种新化合物磷酯酰3-羟基丙腈的合成工艺 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN108484667A true CN108484667A (zh) | 2018-09-04 |
Family
ID=63319112
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810236466.XA Pending CN108484667A (zh) | 2018-03-21 | 2018-03-21 | 一种新化合物磷酯酰3-羟基丙腈的合成工艺 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN108484667A (zh) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1156054A1 (en) * | 1999-02-23 | 2001-11-21 | Ono Pharmaceutical Co., Ltd. | Drugs containing phosphoric acid derivatives as the active ingredient |
| CN105985373A (zh) * | 2015-04-10 | 2016-10-05 | 江苏东南纳米材料有限公司 | 一种制备（r）-1,2-二脂肪酸甘油磷酯酰甘油酯的新方法 |
| WO2017099823A1 (en) * | 2015-12-10 | 2017-06-15 | Modernatx, Inc. | Compositions and methods for delivery of therapeutic agents |
-
2018
- 2018-03-21 CN CN201810236466.XA patent/CN108484667A/zh active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1156054A1 (en) * | 1999-02-23 | 2001-11-21 | Ono Pharmaceutical Co., Ltd. | Drugs containing phosphoric acid derivatives as the active ingredient |
| CN105985373A (zh) * | 2015-04-10 | 2016-10-05 | 江苏东南纳米材料有限公司 | 一种制备（r）-1,2-二脂肪酸甘油磷酯酰甘油酯的新方法 |
| WO2017099823A1 (en) * | 2015-12-10 | 2017-06-15 | Modernatx, Inc. | Compositions and methods for delivery of therapeutic agents |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN105801419A (zh) | 曲前列环素二乙醇胺的合成方法及新颖中间体 | |
| CN102603524B (zh) | 一种醌类衍生物及其制备方法与作为抗菌剂的应用 | |
| CN101463058B (zh) | 羊毛脂烷型三萜化合物海莲酸、其衍生物及其制备方法和用途 | |
| US10618862B2 (en) | Process for preparing (9e, 11z)-9,11-hexadecadienal | |
| CN108484667A (zh) | 一种新化合物磷酯酰3-羟基丙腈的合成工艺 | |
| CN107759475B (zh) | 脱氢枞胺衍生物及其制备方法和应用 | |
| CN103012140B (zh) | 吉法酯的制备方法 | |
| Mull et al. | Production of gliotoxin and a second active isolate by Penicillium obscurum Biourge | |
| CN100480252C (zh) | 蔗糖衍生物及其制法和利用蔗糖衍生物合成三氯蔗糖的方法 | |
| CN107641080B (zh) | 一种含螺环结构的二氢萘酮类衍生物及其制备方法 | |
| CN106045942B (zh) | 一种盐酸普莫卡因的制备方法 | |
| CN104387221B (zh) | 一种培维a酸脱羧体杂质的合成方法 | |
| CN103864747B (zh) | 倒捻子素的全合成方法 | |
| US7897820B2 (en) | Process for preparing erianin | |
| GB2098609A (en) | Process for the preparation of wherein (7E,9Z)-alkadienol derivatives | |
| CN105753902B (zh) | 一种福司氟康唑的制备方法 | |
| CN107325030A (zh) | 一类新型反式芪类抗肿瘤剂 | |
| CN110452199B (zh) | 一种非罗考昔的制备方法 | |
| CN113416142B (zh) | 一种5-ala中间体5-溴乙酰丙酸酯的制备方法 | |
| CN108689805B (zh) | 一种白藜芦醇的制备方法 | |
| Wolfrom et al. | Derivatives of the Aldehydrol Form of Sugars. III. 1 Carbon One Asymmetry | |
| KR950005737B1 (ko) | 징코라이드 혼합물로부터 단성분의 분리방법 | |
| CN111087420A (zh) | 一种1,2-二棕榈酰-sn-甘油-3-磷酸的制备方法 | |
| CN113773221A (zh) | 一种对苯醌类化合物及其制备方法 | |
| CN106279280A (zh) | 一种化合物及其制备方法和应用 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20180904 |