Synthesis of a chiral phospholipase-C and D insensitive membrane probe with excimer emission properties

Synthesis and Properties of Chiral Self-Assembling Lamellar Polydiacetylene Systems with Very-Long-Range Order

“…The coupling constants between these protons and the neighboring methine proton are indicative of the relative orientation of the acyloxy groups on these two carbons. The splittings were similar to those observed in a similar molecule where the acyl chains bore pyrenyl substituents at their termini and were known to be parallel by virtue of the fact that the pyrenyl groups displayed excimer emission . For compound 2, the signals for these methylene protons were two mutually coupled doublets of doublets.…”

“…The synthetic route utilizes the stereocenter in ( S )-3-hydroxybutyrolactone as the source of chirality. The preparation of the lactone has been described earlier, and the steps described here have been demonstrated to preserve the stereocenter . ( S )-3-Hydroxybutyrolactone (51 g, 0.5 mol), N , N -dimethylethylenediamine (44 g, 0.5 mol), and 100 mL of absolute ethanol were mixed and stirred for 24 h. The solvent was removed by rotatory evaporation under reduced pressure.…”

Direct Conversion of (S)-3-Hydroxy-γ-butyrolactone to Chiral Three-Carbon Building Blocks

“…There is one significant advance in the use of an unprotected carbohydrate as a raw material for producing a chiral building block that could be used to gain access to compounds such as 1 − 3 . This is the development of a route to ( S )-3-hydroxy-γ-butyrolactone ( 8 ), a very valuable four-carbon chiral synthon for which a simple, one-step, high-yield route starting from starch, maltose, lactose, maltodextrins, and other 4-linked d -pyranoses has only recently been introduced into the literature. − ( S )-3-Hydroxy-γ-butyrolactone readily undergoes a variety of chemical transformations to yield chiral substituted tetrahydrofurans, amides, lactams, nitriles, and epoxides. This high degree of flexibility as a chiral intermediate makes it a very valuable synthon for the pharmaceutical industry.…”

Taming Carbohydrate Complexity: A Facile, High-Yield Route to Chiral 2,3-Dihydroxybutanoic Acids and 4-Hydroxytetrahydrofuran-2-ones with Very High Optical Purity from Pentose Sugars

“…The S -isomers of 3,4-dihydroxybutanoic acid ( 1 , Chart ) and the corresponding γ-lactone 2 have recently been used in the preparation of a chiral membrane probe, pH-sensitive liposomes, drug intermediates, − advanced two-dimensional supramolecular systems, and azetidinones . These same molecules or close derivatives from ( S )-malic acid (hydroxybutanedioic acid) 3 have been used to prepare a variety of chiral substructures and pharmaceutical intermediates. − Compounds 1 and 2 were obtained by the selective oxidative cleavage of 4-linked hexopyranose sources such as lactose, starch, cellulose, cellobiose, maltose, and maltodextrins . In the preparation of 1 and 2 by this method, the chiral centers are derived from the 5-position of a hexose that always has the d -configuration.…”

“…Despite their availability and chiral richness, carbohydrates are still grossly underutilized as raw materials for fine chemistry. The oxidation of carbohydrates to yield ( S )-3,4-dihydroxybutanoic acid and derivatives ,, is an important step forward in renewable resource chemistry. Here we provide for an expansion of renewable raw material resources and a broader stereochemistry palette which should considerably further our advancement toward a carbohydrate-based chiral chemistry.…”