- Thermal analysis of new glycopolymers derived from monosaccharides
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A novel monomer carrying carbohydrate moiety was prepared by simple reaction of methacrylic acid with 3-O-(2′,3′-epoxy-propyl)-1,2:5,6- di-O-isopropylidene-α-d-glucofuranose. Another d-glucose oligomer was synthesized by the polycondensation of a dicarbox
- Stefan, Liliana-Marinela,Pana, Ana-Maria,Bandur, Geza,Martin, Patrick,Popa, Marcel,Rusnac, Lucian-Mircea
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Read Online
- Nitrosocarbonyl Carbohydrate Derivatives: Hetero Diels-Alder and Ene Reaction Products for Useful Organic Synthesis
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The generation and trapping of two new nitrosocarbonyl intermediates bearing carbohydrate-based chiral substituents is achieved by the mild oxidation of the corresponding nitrile oxides with tertiary amine N -oxides. Their capture with suitable dienes and alkenes afforded the corresponding hetero Diels-Alder cycloadducts and ene adducts from fair to excellent yields. The entire methodology looks highly promising by the easy conversion of aldoximes into hydroxymoyl halides, widening the access to nitrosocarbonyls, versatile tools in organic synthesis.
- Corti, Marco,Leusciatti, Marco,Moiola, Mattia,Mella, Mariella,Quadrelli, Paolo
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p. 574 - 586
(2020/10/06)
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- Metal-free [3+2] cycloaddition of glycosyl olefinic ester with in situ generated CF3CHN2: Access to CF3-substituted pyrazoline glycoconjugates
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An efficient [3 + 2] cycloaddition of glycosyl olefinic ester with in situ generated CF3CHN2 for the syntheses of CF3-substituted pyrazoline glycoconjugate has been developed. This mild, one-pot reaction condition avoiding the use of metallic catalyst and additive will be useful in the pharmaceutical industry. This reaction features are the broad substrate scope, good functional group tolerance with good to high yields.
- Javed,mandal, Pintu Kumar
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supporting information
(2020/07/20)
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- Synthesis of helicobacter-pylorus O2 serotype O antigen oligosaccharide compound
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The invention discloses discloses synthesis of a helicobacter-pylorus O2 serotype O antigen oligosaccharide compound, and belongs to the field of organic synthesis. According to the synthesis, helicobacter-pylorus O2 serotype O-antigen disaccharide to tet
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Paragraph 0087; 0088; 0089; 0091
(2019/06/07)
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- MODIFIED NUCLEOSIDE PHOSPHORAMIDITES
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The present disclosure relates to compounds and compositions containing 5'-phosphoramidite nucleoside monomers of formulae (I) and (II), and methods of making and use, wherein the substituents are as defined in the appended claims.
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Paragraph 0209; 0243
(2019/04/11)
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- Synthesis and antiplasmodial activity of purine-based C-nucleoside analogues
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A series of homologous C-nucleoside mimics have been synthesized via an efficient and facile synthetic protocol involving the conjugate addition of purine to sugar derived olefinic ester in good yields. The synthesized compounds were evaluated for their a
- Singh, Kartikey,Joshi, Prince,Mahar, Rohit,Baranwal, Pragati,Shukla, Sanjeev K.,Tripathi, Renu,Tripathi, Rama Pati
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p. 1232 - 1238
(2018/08/01)
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- I2/PPh3-mediated facile synthesis of glycoconjugated N-acylbenzotriazoles
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A well-stabilized method for synthesis of N-acylbenzotriazoles from carboxylic acids using I2/PPh3 in anhydrous dichloromethane has been extended in glycochemistry to synthesize glycoconjugated N-acylbenzotriazoles with high yields at room temperature in 2-hour reaction time.
- Singh, Mala,Agrahari, Anand K.,Mishra, Nidhi,Singh, Anoop S.,Tiwari, Vinod K.
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p. 125 - 132
(2018/09/14)
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- Preparation method for 1,2,5,6-di-isopropylidene-3-O-benzyl-alpha-D-furan glucoside
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The invention provides a preparation method for 1,2,5,6-di-isopropylidene-3-O-benzyl-alpha-D-furan glucoside. The preparation method comprises the following steps: adding 1,2,5,6-di-isopropylidene-alpha-D-glucofuranose, alkali and an organic solvent into a reaction container provided with a reflowing manifold, and carrying out a reflowing dehydration reaction; when carrying out the reaction until no water is evaporated out from the reflowing manifold, dropwise adding a benzylation reagent; after carrying out dropwise adding, continually carrying out a reflowing dehydration and heat-preservation reaction until the reaction is finished; and then carrying out after-treatment on a reaction solution to obtain a product. The preparation method provided by the invention has the advantages of low cost, high product yield, high quality, low unit consumption of raw materials and solvents, simple and feasible after-treatment technology, less wastewater amount and easiness for realizing industrialization.
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Paragraph 0031-0050
(2018/03/13)
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- Stereodivergent synthesis of right- and left-handed iminoxylitol heterodimers and monomers. Study of their impact on β-glucocerebrosidase activity
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A library of dimers and heterodimers of both enantiomers of 2-O-alkylated iminoxylitol derivatives has been synthesised and evaluated on β-glucocerebrosidase (GCase), the enzyme responsible for Gaucher disease (GD). Although the objective was to target simultaneously the active site and a secondary binding site of the glucosidase, the (-)-2-iminoxylitol moiety seemed detrimental for imiglucerase inhibition and no significant enhancement was obtained in G202R, N370S and L444P fibroblasts. However, all compounds having at least one (+)-2-O-alkyl iminoxylitol are GCase inhibitors in the nano molar range and are significant GCase activity enhancers in G202R fibroblats, as confirmed by a decrease of glucosylceramide levels and by co-localization studies.
- Stauffert, Fabien,Serra-Vinardell, Jenny,Gómez-Grau, Marta,Michelakakis, Helen,Mavridou, Irene,Grinberg, Daniel,Vilageliu, Llu?sa,Casas, Josefina,Bodlenner, Anne,Delgado, Antonio,Compain, Philippe
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supporting information
p. 3681 - 3705
(2017/07/07)
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- Synthesis of novel macrocyclic crown ethers from D-glucose
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A simple and efficient synthetic protocol for an easy access of carbohydrate-linked crown ethers from cheap and readily available D-glucose in good yields has been devised. The base-mediated cyclization of sugar-linked bis-iodo podands in CH3CN
- Mishra, Amrita,Mishra, Nidhi,Tiwari, Vinod K.
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p. 238 - 248
(2016/09/04)
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- Synthetic heparin pentasaccharides
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Preparation and use of synthetic monosaccharides, disaccharides, trisaccharides, tetrasaccharides and pentasaccharides useful for the preparation of synthetic heparinoids.
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Page/Page column 29; 40; 41
(2016/02/12)
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- Metal free synthesis of morpholine fused [5,1-c] triazolyl glycoconjugates via glycosyl azido alcohols
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A series of diverse glycosyl 1,2-azido alcohols, obtained from readily available carbohydrates, were converted to structurally varied rare and novel sugar derived morpholine fused [5,1-c]-triazoles via a one-pot strategy. After incorporating a propargyl functionality at the hydroxyl group of the sugar derived 1,2-azido alcohols, the resulting in situ generated azido-alkyne affords numerous C- and O-glycosyl bicyclic ring systems with medicinal value via a metal free cycloaddition reaction. The structures of all the developed molecules have been elucidated using 1H NMR, 13C NMR, IR and MS spectroscopy.
- Mishra, Kunj B.,Shashi, Somesh,Tiwari, Vinod K.
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p. 86840 - 86848
(2015/11/03)
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- Design and synthesis of carbohydrate based medium sized sulfur containing benzannulated macrocycles: Applications of Sonogashira and Heck coupling
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Palladium catalyzed intramolecular Sonogashira and Heck coupling reactions have been applied for diversity-oriented synthesis of sulfur containing carbohydrate based medium sized ring macrocycles. The process involves design and synthesis of building bloc
- Hussain, Altaf,Yousuf, Syed Khalid,Sharma, Deepak K.,Mallikharjuna Rao,Singh, Baldev,Mukherjee, Debaraj
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supporting information
p. 5517 - 5524
(2013/07/05)
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- Stereoselective synthesis of spiro-β-lactams using d-(+)-glucose derived chiral pool: remarkable influence of the torquoelectronic effect
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Diastereoselective synthesis of spiro-β-lactams via [2+2] cycloaddition reaction of imines and chiral ketenes is described. The chiral ketene was prepared from commercially available, inexpensive d-glucose. Although, theoretically four diastereomers are p
- Chincholkar,Puranik, Vedavati G.,Deshmukh
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p. 9179 - 9187
(2008/02/10)
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- An epoxide derived from D-glucose as the key intermediate for penaresidine and sphingolipids synthesis
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A multigram-scale synthesis of 3R,4R,5R 3,5-dibenzyloxy-4-p- methoxybenzyl-1,2-epoxypentane and its use as intermediate for sphingolipids, penazeridine and penazetidine synthesis are described.
- Beauhaire, Josiane,Ducrot, Paul-Henri
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p. 2443 - 2456
(2007/10/03)
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- IRIDOID AND PHENOLIC GLYCOSIDES FROM HARPAGOPHYTUM PROCUMBENS
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Key Word Index - Harpagophytum procumbens; Pedaliaceae; iridoid and phenolic glycosides; synthesis.A novel bioside, β-(3',4'-dihydroxyphenyl)ethyl-O-α-L-rhamnopyranosyl(1 -> 3)-β-D-glucopyranoside, was obtained from the secondary roots of Harpagophytum procumbens.It is accompained by the known iridoid glucosides harpagoside, procumbide, and its 6'-O-p-coumaroyl ester, and phenolic glycosides, acteoside and isoacteoside, the latter pair being obtained from H. procumbens for the first time.The structures of these metabolites were differentiated by high resolution NMR studies, while that of the bioside is additionally supported by synthesis.
- Burger, Johann F. W.,Brandt, E. Vincent,Ferreira, Daneel
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p. 1453 - 1458
(2007/10/02)
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- SYNTHESES OF 1,5-DIDEOXY-1,5-IMINO-D-MANNITOL FROM D-MANNOSE AND D-GLUCOSE
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Unambigous enantiospecific syntheses of 1,5-dideoxy-1,5-imino-D-mannitol (LU1, 1-deoxy-mannojirimycin) are reported (i) from D-mannose via hydrogenation of a 5-azido-5-deoxy mannose, and (ii) from D-glucose, in which the key step involves nucleophilic substitution of a trifluoromethanesulphonyl group from C-2 of D-glucose.
- Fleet, G. W. J.,Gough, M. J.,Shing, T. K. M.
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p. 4029 - 4032
(2007/10/02)
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- SYNTHESIS OF A NOVEL PLATELET ACTIVATING FACTOR CONGENER FROM DIACETONE GLUCOSE
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A synthesis of the novel PAF congener 2 via a monosaccharide template is described.
- Anderson, R.C.,Nabinger, R.C.
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p. 2741 - 2744
(2007/10/02)
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