1941-52-2Relevant articles and documents
Prodrugs of L-Cysteine as Protective Agents against Acetaminophen-Induced Hepatotoxicity. 2-(Polyhydroxyalkyl)- and 2-(Polyacetoxyalkyl)thiazolidine-4(R)-carboxylic Acids
Roberts, Jeanette C.,Nagasawa, Herbert T.,Zera, Richard T.,Fricke, Robert F.,Goon, David J. W.
, p. 1891 - 1896 (1987)
Eight prodrugs of L-cysteine (1a-h) were synthesized by the condensation of the sulfhydryl amino acid with naturally occurring aldose monosaccharides containing three, five, and six carbon atoms.The resulting 2-(polyhydroxyalkyl)thiazolidine-4(R)-carboxylic acids (TCAs) are capable of releasing L-cysteine and the sugars by nonenzymatic ring opening and hydrolysis.Thus, when added to rat hepatocyte preparations in vitro, these TCAs (1.0 mM) raised cellular gluthatione (GSH) levels 1.2-2.1-fold relative to controls.On the basis of this finding, the cysteine prodrugs were tested as protective agents against acetaminophen-induced hepatotoxicity in a mouse model.The TCA derived from D-ribose and L-cysteine (RibCys, 1d) showed the greatest therapeutic promise of the series, with a 100percent (12/12) survival profile compared to 17percent without treatment.However, the degree of stimulation of GSH production in rat hepatocytes by these prodrugs did not correlate with the extent of protection afforded in mice, suggesting that pharmacokinetic parameters must supervene in vivo.To evaluate the effect of increased lipid solubility, we prepared prodrugs 2a-c by using peracetylated aldehydic sugars in the condensation reaction.These compounds, however, displayed acute toxicity to mice, possibly due to liberation of the acetylated sugars themselves.Nevertheless, the efficacy of the unacetyleted TCAs, and RibCys (1d) in particular, suggests that the prodrug approach for the delivery of L-cysteine to the liver represents a viable means of augmenting existing detoxication mechanisms in protecting cells against xenobiotic substances that are bioactivated to toxic, reactive metabolites.
Bromodimethylsulfonium bromide (BDMS) mediated dithioacetalization of carbohydrates under solvent-free conditions
Khan, Abu T.,Khan, Md. Musawwer
, p. 2139 - 2145 (2010)
A variety of diethyl dithioacetals of sugars can be prepared in very good yields by the reaction of various monosaccharides with ethanethiol in the presence of 3 mol % bromodimethylsulfonium bromide (BDMS) at 0-5 °C. Similarly, dipropyl dithioacetal derivatives can also be obtained in good yields using propanethiol under identical reaction conditions. These dithioacetal derivatives were characterized by per-O-acetylation using silica gel-supported perchloric acid. The significant features of the present protocol are good-to-excellent yields, mild, clean, and solvent-free reaction conditions. This method is extremely suitable for the large-scale preparation of dithioacetal derivatives of various sugars.
The invention of radical reactions. Part XXXVI. Synthetic studies related to 3-deoxy-D-manno-2-octulosonic acid (KDO)
Barton,Jaszberenyi,Liu,Shinada
, p. 2717 - 2726 (1996)
An application of the Barton ester based radical reactions in carbohydrate chemistry is described. The chain-elongation reaction with ethyl α-trifluoroacetoxy acrylate 2, followed by treatment with phenylhydrazine provided 3-deoxy-α-hydrazono-octulosonates 8a,b derivatives of KDO and its gluco-isomer in good yield.
Regioselective Synthesis of Difluorinated C-Furanosides Involving a Debenzylative Cycloetherification
Delbrouck, Julien A.,Bochatay, Valentin N.,Tikad, Abdellatif,Vincent, Stéphane P.
supporting information, p. 5562 - 5566 (2019/08/01)
A highly regioselective synthesis of valuable gem-difluorinated C-furanosides from unprotected aldoses via a debenzylative cycloetherification (DBCE) reaction induced by diethylaminosulfur trifluoride is descibed. The scope and limitations of this DBCE reaction are described using a series of commercially available pentoses and hexoses to afford, without selective protection/deprotection sequences, the corresponding gem-difluorinated C-furanosides in moderate to good yields.
Efficient and regioselective synthesis of γ-lactone glycosides through a novel debenzylative cyclization reaction
Delbrouck, Julien A.,Tikad, Abdellatif,Vincent, Stéphane P.
supporting information, p. 9845 - 9848 (2018/09/10)
An efficient and regioselective approach for the construction of synthetically important γ-lactone glycosides is reported from unprotected aldoses through a new debenzylative lactonization (DBL) reaction. The scope and limitations of this DBL reaction are described starting from a series of commercially available hexoses (l-fucose, d-galactose, d-glucose) and pentoses (d-arabinose, d-ribose, d-lyxose, d-xylose) to afford the corresponding γ-lactones in good yields and without concomitant δ-lactone formation.
Dapagliflozin impurity synthesis method
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Paragraph 0004; 0018-0020, (2017/03/14)
The invention discloses a dapagliflozin impurity synthesis method. The synthesis method includes: using D-glucose as a raw material; subjecting the D-glucose to reactions of aldehyde group protection through ethanethiol, benzyl group adding, ethanethiol removal, condensation and benzyl group removal to obtain dapagliflozin impurities. A basis is provided for study of dapagliflozin related substances.
Structure-activity relationship studies on acremomannolipin A, the potent calcium signal modulator with a novel glycolipid structure 2: Role of the alditol side chain stereochemistry
Tsutsui, Nozomi,Tanabe, Genzoh,Gotoh, Genki,Morita, Nao,Nomura, Naohisa,Kita, Ayako,Sugiura, Reiko,Muraoka, Osamu
, p. 945 - 959 (2014/02/14)
Five alditol analogs 1b-1f of a novel glycolipid acremomannolipin A (1a), the potential Ca2+ signal modulator isolated from Acremonium strictum, were synthesized by employing a stereoselective β-mannosylation of appropriately protected mannose with five hexitols with different stereochemistry, and their potential on modulating Ca2+ signaling were evaluated All these analogs were more potent compared to the original compound 1a, and proved that mannitol stereochemistry of 1a was not critical for the potent calcium signal modulating
Synthesis of 2,3,4,5-tetra-O-methyl-D-glucono-1,6-lactone as a monomer for the preparation of copolyesters
Molina Pinilla, Inmaculada,Bueno Martinez, Manuel,Galbis, Juan A.
, p. 549 - 555 (2007/10/03)
2,3,4,5-Tetra-O-methyl-D-glucono-1,6-lactone has been prepared as a crystalline compound in acceptable yield by two different routes. An initial assay of copolymerization with L-lactide by ring-opening polymerization was carried out. The incorporation of the carbohydrate monomer into the polymer chain was about 2%.
Liquid-Crystalline D-Glucose Dialkyl Acetals and Dodecyl D-Glucofuranosides
Tietze, Lutz F.,Boege, Kai,Vill, Volkmar
, p. 1065 - 1068 (2007/10/02)
Two new systems of liquid crystalline glucose derivatives 5a-d, 6a, b are prepared, studied and compared with reference compounds.The α- and β-D-dodecyl glucofuranosides 6a, b show smectic A phases.The clearing points of the furanosides are of the same magnitude as those of the pyranosides.The alkyl glucose acetals 5a-d show columnar discotic phases.The clearing points are about 30 deg C lower than those of the corresponding thioacetals. - Key Words: Acetals / Amphiphiles / Carbohydrates / Glucosides / Liquid crystals
