Homo-C-nucleoside analogs IV. Synthesis of 4-(2,5-anhydro-D-altro-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole homo-C-nucleoside. CD assignment of the absolute configuration of the carbon bridge

被引：1

作者：

Sallam, Mohammed A. E. ^{[1
]}

机构：

[1] Univ Alexandria, Dept Chem, Fac Sci, Alexandria, Egypt

来源：

CHIRALITY | 2017年 / 29卷 / 01期

关键词：

1,2,3-triazoles; anomeric configuration; carbon bridge chirality; circular dichroism; homo-C-nucleosides; ORAL BIOAVAILABILITY; INTESTINAL-ABSORPTION; DRUG ABSORPTION; PERMEABILITY; RAT; PERFUSION;

D O I：

10.1002/chir.22663

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Dehydrative cyclization of 4-(D-altro-pentitol-1-yl)2-phenyl-2H-1,2,3-triazole in basic medium with one moler equivalent of p-toluene sulfonyl chloride in pyridine solution gave the homo-C-nucleoside 4-(2,5-anhydro-D-altro-1-yl)-2-phenyl-2H-1,2,3-triazole. The structure and anomeric configuration was determined by acylation, nuclear magnetic resonance (NMR), and mass spectroscopy. The stereochemistry at the carbon bridge of homo-C-nucleoside 2-phenyl-2H-1,2,3-triazoles was determined by circular dichroism (CD) spectroscopy.

引用

页码：33 / 37

页数：5

共 6 条

[1] Homo-C-nucleoside analogs III. Studies on the base-catalyzed dehydrative cyclization of 4-(D-manno-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole
Sallam, Mohammed A. E.
CARBOHYDRATE RESEARCH, 2010, 345 (15) : 2233 - 2238
[2] CD and NMR assignment of the anomeric configuration of 4-(5-deoxy-α,β-L-arabinofuranosyl)-2-phenyl-2H-1,2,3-triazole C-nucleoside analogs
Sallam, Mohammed A. E.
CARBOHYDRATE RESEARCH, 2010, 345 (03) : 341 - 345
[3] Acid-catalyzed dehydrative cyclization of 4-(D-galacto-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole.: Synthesis and anomeric configuration of D-lyxo-C-nucleoside analogs
Sallam, MAE
Megid, SMEA
Townsend, LB
CARBOHYDRATE RESEARCH, 2001, 330 (01) : 53 - 63
[4] Chiroptical Assignment of the Anomeric Configuration of 4-(α,β-D-lyxopyranosyl)- and 4-(α,β-D-lyxofuranosyl)-2-phenyl-2H-1,2,3-Triazole C-Nucleoside Anomeric Pairs: Extension of the CD Triazole Rule
Sallam, Mohammed A. E.
JOURNAL OF CARBOHYDRATE CHEMISTRY, 2009, 28 (09) : 498 - 505
[5] Circular dichroism as a reliable tool for anomeric assignment of glycosyl-2-phenyl-2H-1,2,3-triazole C-nucleoside analogs.: A rule for prediction of their anomeric configuration
Sallam, Mohammed A. E.
CHIRALITY, 2006, 18 (10) : 790 - 798
[6] Studies on the dehydrative cyclization of epimeric 4-(L-xylo and L-lyxo-tetritol-1-yl)-2-phenyl-2H-1,2,3-triazoles.: Circular dichroism and NMR assignment of the formed anomeric C-nucleoside L-threofuranosyl triazole analogs
Sallam, MAE
Louis, FF
CHIRALITY, 2004, 16 (05) : 331 - 335

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