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
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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。
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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 |
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| 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 |
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