[Development of unprotected syntheses in aqueous media].

Synthesis of a Phosphonate Analog of Sialic Acid (Neu5Ac) Using Indium-Mediated Allylation of Unprotected Carbohydrates in Aqueous Media

Sialic acid (Neu5Ac, 1), a constituent of sialoglycoproteins1 and gangliosides,2 mediates a number of intercellular and cell-virion recognition events.3 Analogs of sialic acid are interesting as potential inhibitors for medicinally important target proteins, such as neuraminidase of the influenza virus.4 The syntheses of sialic acid and its analogs have been the subject of extensive research.5 ...

Cross-coupling reactions of unprotected halopurine bases, nucleosides, nucleotides and nucleoside triphosphates with 4-boronophenylalanine in water. Synthesis of (purin-8-yl)- and (purin-6-yl)phenylalanines.

An expeditious and highly efficient single-step methodology for the introduction of a phenylalanine moiety into position 8 and 6 of the purine scaffold was developed based on aqueous-phase Pd-catalysed Suzuki-Miyaura cross-coupling reactions of unprotected 4-boronophenylalanine with 8-bromo- or 6-chloropurines. The scope of the methodology was demonstrated by syntheses of unprotected (adenin-8-...

Efficient synthesis of unprotected C-5-aryl/heteroaryl-2'-deoxyuridine via a Suzuki-Miyaura reaction in aqueous media.

Following our previous results on an environmentally benign one-pot Sonogashira-cyclization protocol to obtain substituted furopyrimidine nucleosides under aqueous conditions, we investigate herein the Suzuki-Miyaura cross-coupling reactions of aryl and heteroaryl derivatives at the C5 position of unprotected 2'-deoxyuridine in the same media with a common catalyst system avoiding exotic ligand...

Synthesis of a Phosphonate Analog of Sialic Acid (NeuSAc) Using Indium-Mediated Allylation of Unprotected Carbohydrates in Aqueous Media

Syntheses and properties of water-soluble Nile Red derivatives.

Nile Red (compound A) fluoresces at about 530 nm with good quantum yields in apolar solvents. In more polar ones its fluorescence emission shows a dramatic, and potentially useful, shift to about 640 nm, but its quantum yield is significantly reduced. Further, Nile Red has a very poor solubility in aqueous media. The hypothesis tested in this paper is that Nile Red derivatives that incorporate ...