Synthesis of an octasubstituted galactose zinc(II) phthalocyanine
Synthesis of an octasubstituted galactose zinc(II) phthalocyanine
复制标题
DOI：
10.1016/j.tetlet.2008.12.015
复制
发表时间：
2009-02-25
影响因子：
1.8
通讯作者：
Ziegler, Thomas
中科院分区：
文献类型：
--
作者：
Iqbal, Zafar;Hanack, Michael;Ziegler, Thomas
以双丙酮半乳糖I和4，5-二氟邻苯二甲腈（2）为原料，经SNAr反应合成了4，5-二（1，2：3，4-二-O-异亚丙基-α-D-吡喃半乳糖-6-基）邻苯二甲腈（3），收率96%。3通过其异吲哚啉衍生物4实现环四聚，以29%的产率提供外围八取代的半乳糖酞菁锌（II）5。5脱保护得到高度水溶性的八取代半乳糖酞菁锌（II）6，产率为81%，其将用作光动力疗法中的光敏剂。(C)2008爱思唯尔有限公司保留所有权利。
4,5-Bis(1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranos-6-yl)phthalonitrile (3) was prepared by SNAr reaction of diacetone galactose I and 4,5-difluorophthalonitrile (2) in 96% yield. Cyclotetramerization of 3 was achieved via its isoindoline derivative 4, affording the peripherally octasubstituted galactose zinc(II) phthalocyanine 5 in 29% yield. Deprotection of 5 gave the highly water soluble octasubstituted galactose zinc(II) phthalocyanine 6 in 81% yield which will be applied as a photosensitizer in photodynamic therapy. (C) 2008 Elsevier Ltd. All rights reserved.