- Synthesis of Anemoclemosides A and B, Two Saponins Isolated from Anemoclema glaucifolium
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Steroidal and triterpenoid saponins are attractive for their wide-ranging pharmacological properties. The triterpenoid saponins Anemoclemoside A and B are root constituents of the Chinese folk medicinal plant Anemoclema glaucifolium (Ranunculaceae). Both
- Bouillon, Marc E.,Bertocco, Katia,Bischoff, Laura,Buri, Michelle,Davies, Lucy R.,Wilkinson, Elizabeth J.,Lahmann, Martina
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supporting information
p. 7470 - 7473
(2020/12/01)
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- COMPOSITIONS AND METHODS FOR THE TREATMENT OF METABOLIC DISEASES
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The invention relates to the compounds of formula I, formula II and formula III or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula I, formula II or formula III; and methods for treating or preventing metabolic diseases may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection. Such compositions may be used to treatment of phenylketonuria, cardiovascular disease, autism, ADHD, hypertension, endothelial dysfunction and chronic kidney disease.
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Paragraph 0168; 0169; 0170
(2015/11/18)
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- The first convergent total synthesis of penarolide sulfate A2, a novel α-glucosidase inhibitor
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Penarolide sulfate A2, a 31-membered macrolide encompassing a proline residue and three sulfate groups, was firstly synthesized in 16 linear steps with 4.8% overall yield. Three consecutive stereogenic centers in penarolide sulfate A2 were efficiently derived from natural chiral template l-arabinose. The crucial assembly reactions included Brown asymmetric allylation, olefin cross-metathesis, alkyne-epoxide coupling, and macrolactamization. The anti-yeast α-glucosidase activities of penarolide sulfate A2 and its fully desulfated derivative were examined showing IC50 values of 4.87 and 10.74 μg mL-1, respectively.
- Gao, Yangguang,Shan, Qiuli,Liu, Jun,Wang, Linlin,Du, Yuguo
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p. 2071 - 2079
(2014/03/21)
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- Bromodimethylsulfonium bromide (BDMS) mediated dithioacetalization of carbohydrates under solvent-free conditions
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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.
- Khan, Abu T.,Khan, Md. Musawwer
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experimental part
p. 2139 - 2145
(2010/11/04)
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- Synthesis of substituted imidazolo[1,2-α]piperidinoses and their evaluation as glycosidase inhibitors
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The synthesis of substituted imidazolo[1,2-α]-L-arabino-piperidinoses is reported. The substituents are methyl, phenylmethyl, phenylethyl, cyclohexylethyl, pyridinylethyl, piperidinylethyl, phenylpropyl and hydroxymethyl. All substituents are connected to
- Dubost, Estelle,Le Nouen, Didier,Streith, Jacques,Tarnus, Celine,Tschamber, Theophile
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p. 610 - 626
(2007/10/03)
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- Studies on enolization of aldehydo-aldose derivatives
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Acetylation of the 2,3-O-isopropylidene derivative (1) of d-glyceraldehyde with hot acetic anhydride in the presence of sodium acetate give a mixture of (Z)- and (E)-enol acetates (2 and 3), together with the acetylated racemic aldehydrol (4) of 1. Likewise, the acyclic aldehydo 2,3:4,5-diisopropylidene acetals of d- and l-arabinose, d-xylose, and d-ribose underwent conversion into enol acetates, with the (Z) isomers preponderating, and convertible photochemically into the corresponding (E) isomers. Under other conditions of acetylation, the aldehydo derivatives were converted into the corresponding aldehydrol diacetates.
- Eitelman, Stephen J.,Horton, Derek
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p. 2658 - 2668
(2007/10/03)
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- Practical synthesis of D-[1-13C]mannose, L-[1-13C] and L-[6-13C]fucose
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The chemical synthesis of 13C-labeled mannose and fucose is important for the preparation of molecular probes used in the conformational study of the oligosaccharide portions of glycoproteins. A new method for the synthesis of the title [1-sup
- Sato, Ken-Ichi,Akai, Shoji,Youda, Hiroki,Kojima, Masaru,Sakuma, Mayumi,Inaba, Shu-Ichirou,Kurosawa, Kyota
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p. 237 - 243
(2007/10/03)
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- Short de novo synthesis of fully functionalized uronic acid monosaccharides
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(Chemical Equation Presented) Short and Sweet: A convergent route leads to orthogonally protected D-glucuronic and L-iduronic acid thioglycoside building blocks, commonly used in heparin oligosaccharide assembly (see scheme). Rapid access to substantial q
- Timmer, Mattie S. M.,Adibekian, Alexander,Seeberger, Peter H.
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p. 7605 - 7607
(2007/10/03)
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- Increasing the inhibitory potency of L-arabino-imidazolo-[1,2]-piperidinose towards β-D-glucosidase and β-D-galactosidase
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The synthesis of some potent inhibitors of two retaining β-glycosidases was achieved by introducing aglycon-mimics into the imidazole moiety of L-arabino azasugar 1. The strongest inhibition was observed with the phenyl-ethyl substituent at C(2) of 1 agai
- Dubost, Estelle,Tschamber, Théophile,Streith, Jacques
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p. 3667 - 3670
(2007/10/03)
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- Cyano/diallylamine additions to glycoside and nucleoside aldehydes and its application to the synthesis of polyoxin L and uracil polyoxin C
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Three efficient, high yielding syntheses of precursors (1) of carbamoylpolyoxamic acid from L-arabinose, based on the simultaneous addition of the acid and amine functionalities, are described. Utilizing the same methodology and uridine as the starting ma
- Kutterer, Kristina M. K.,Just, George
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p. 1409 - 1420
(2007/10/03)
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- First and stereoflexible synthesis of vinylogous taxol side chains
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First and stereoflexible synthesis of two vinylogous side chains of Taxol from readily available L-arabinose and methyl 3-phenylglycidate as starting materials is described.
- Yadav,Chandrasekhar,Sasmal, Pradip K.
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p. 8765 - 8768
(2007/10/03)
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- Process for preparing 5-deoxy-L-arabinose
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The process for preparing 5-deoxy-arabinose comprises reacting 5-tosyl-L-arabinose-dialkylmercaptal with NaBH4 in DMSO to give 5-deoxy-L-arabinose-dialkylmercaptal and then reacting the obtained 5-deoxy-L-arabinose-dialkylmercaptal with hydrochloric acid in DMSO. According to the process, 5-deoxy-L-arabinose can be obtained in a high yield without employing heavy metal such as mercury.
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- SYNTHESIS OF OPTICALLY ACTIVE PSEUDO-α-D-GLUCOSE AND PSEUDO-β-L-ALTROSE
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Optically active two pseudo-sugars, pseudo-α-D-glucose and pseudo-β-L-altrose have been synthesized by cyclization of 2,3,4-tri-O-benzyl-5-deoxy-5-iodo-L-arabinose with dimethyl malonate in the presence of sodium hydride as a key reaction.
- Suami, Tetsuo,Tadano, Kin-ichi,Kameda, Yukiaki,Iimura, Youichi
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p. 1919 - 1922
(2007/10/02)
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