C-glycosylated pyrroles and their application in dipyrromethane and porphyrin synthesis

被引：3

作者：

Sollert, Carina ^{[1
]}

Kocsi, Daniel ^{[1
]}

Jane, Reuben T. ^{[1
]}

Orthaber, Andreas ^{[1
]}

Borbas, K. Eszter ^{[1
]}

机构：

[1] Uppsala Univ, Dept Chem, Angstrom Lab, Box 523, S-75120 Uppsala, Sweden

来源：

JOURNAL OF PORPHYRINS AND PHTHALOCYANINES | 2021年 / 25卷 / 7-8期

基金：

瑞典研究理事会;

关键词：

glycosylation; dipyrromethane; BODIPY; tolyporphin analogues; NATURAL-PRODUCT; BIOLOGICAL EVALUATION; TOLYPORPHIN; BEARING; N-(TRIISOPROPYLSILYL)PYRROLE; RESISTANCE; INDOLES; ANALOGS; COPPER;

D O I：

10.1142/S1088424621500723

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Pyrrole C-glycosylated in either the 2- or the 3-position could be prepared by the acid-catalyzed reaction between trichloroacetimidate glycosyl donors and pyrrole, or N-phenyl-trifluoroacetimidate glucosyl donor and N-TIPS pyrrole, respectively. Pyrroles carrying glucose, mannose, galactose and lactose in the 2-position, and glucose in the 3-position were obtained. The configurations of the products could be assigned using a combination of 1D and 2D NMR spectroscopy. A number of undesired background reactions yielding a variety of stereo- and regioisomers were identified; in several cases these could be eliminated. Glycosylpyrroles could be incorporated into mono- and diglycosylated dipyrromethanes, a diglycosylated BODIPY dye, and a monoglycosylated Zn(II) porphyrin without damaging the sugar unit.

引用

页码：741 / 755

页数：15

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