Expeditious synthesis of glycosylated phthalocyanines
Expeditious synthesis of glycosylated phthalocyanines
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DOI：
10.1055/s-2007-983753
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发表时间：
2007-07-17
影响因子：
2.6
通讯作者：
Ziegler, Thomas
中科院分区：
文献类型：
--
作者：
Alvarez-Mico, Xavier;Calvete, Mario J. F.;Ziegler, Thomas
通过4-硝基邻苯二甲腈与乙酰基保护的葡萄糖和1-硫代葡萄糖的亲核芳香取代反应，以几乎定量的产率制备了葡萄糖、半乳糖、乳糖和纤维二糖系列中的3，4-二氰基苯基O-和S-糖苷。类似地，2-（3，4-二氰基苯氧基）乙基2，3，4，6-四-O-乙酰基-β-D-葡萄糖-和-半乳糖-吡喃糖苷通过2-（甲苯磺酰氧基）乙基2，3，4，6-四-O-乙酰基-β-D-葡萄糖-和-半乳糖-吡喃糖苷与3，4-二氰基苯酚的亲核取代反应分别以82%和94%的产率得到2-（3，4-二氰基苯氧基）乙基2，3，4，6-四-O-乙酰基-β-D-葡萄糖-和半乳糖-吡喃糖苷。所有的糖苷被脱乙酰化和四聚成相应的糖基化的锌（II）酞菁，而无需进一步纯化，使用模板缩合，产率为42-54%。
3,4-Dicyanophenyl O- and S-glycosides in the gluco, galacto, lacto, and cellobiose series were prepared in virtually quantitative yield through nucleophilic aromatic substitution of 4-nitrophthalonitrile with acetyl-protected glycoses and 1-thio-glycoses. Similarly, 2-(3,4-dicyanophenoxy)ethyl 2,3,4,6-tetra-O-acetyl-beta-D-gluco- and galacto-pyranosides were obtained by nucleophilic substitution of 2-(tosyloxy)ethyl 2,3,4,6-tetra-O-acetyl-beta-D-gluco- and -galactopyranoside with 3,4-dicyanophenol in 82% and 94% yields, respectively. All glycosides were deacetylated and tetramerized to the corresponding glycosylated zinc(II) phthalocyanines without further purification using a template condensation in 42-54% yields.