- Establishment of Guidelines for the Control of Glycosylation Reactions and Intermediates by Quantitative Assessment of Reactivity
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Stereocontrolled chemical glycosylation remains a major challenge despite vast efforts reported over many decades and so far still mainly relies on trial and error. Now it is shown that the relative reactivity value (RRV) of thioglycosides is an indicator for revealing stereoselectivities according to four types of acceptors. Mechanistic studies show that the reaction is dominated by two distinct intermediates: glycosyl triflates and glycosyl halides from N-halosuccinimide (NXS)/TfOH. The formation of glycosyl halide is highly correlated with the production of α-glycoside. These findings enable glycosylation reactions to be foreseen by using RRVs as an α/β-selectivity indicator and guidelines and rules to be developed for stereocontrolled glycosylation.
- Chang, Chun-Wei,Wu, Chia-Hui,Lin, Mei-Huei,Liao, Pin-Hsuan,Chang, Chun-Chi,Chuang, Hsiao-Han,Lin, Su-Ching,Lam, Sarah,Verma, Ved Prakash,Hsu, Chao-Ping,Wang, Cheng-Chung
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supporting information
p. 16775 - 16779
(2019/11/03)
-
- Synthesis of MeON-neoglycosides of digoxigenin with 6-deoxy- and 2,6-dideoxy-D-glucose derivatives and their anticancer activity
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Cardiac glycosides show anticancer activities and their deoxy-sugar chains are vital for their anticancer effects. In order to study the structure-activity relationship (SAR) of cardiac glycosides toward cancers and get more potent anticancer agents, a series of MeON-neoglycosides of digoxigenin was synthesized and evaluated. First, ten 6-deoxy- and 2,6-dideoxy-D-glucopyranosyl donors were synthesized starting from methyl α-D-glucopyranoside and 2-deoxy-D-glucose. Meanwhile, the digoxigenin was obtained by acidic hydrolysis of commercially available digoxin as glycosyl acceptor. Then, a 22-member MeON-neoglycoside library of digoxigenin was successfully synthesized by neoglycosylation method. Finally, the induction of Nur77 expression and its translocation from the nucleus to cytoplasm together with cytotoxicity of these MeON-neoglycosides were evaluated. The SAR analysis revealed that C3 glycosylation is required for their induction of Nur77 expression. Moreover, some MeON-neoglycosides (2b and 8b) could significant induce the expression of Nur77 and its translocation from the nucleus to cytoplasm. However, these compounds showed no inhibitory effects on the proliferation of cancer cells, suggesting that they may not induce apoptosis of NIH-H460 cancer cells and their underlying potential and application toward cancer cells deserves future study.
- Wang, Dong-dong,Li, Xiao-san,Bao, Yu-zhou,Liu, Jie,Zhang, Xiao-kun,Yao, Xin-sheng,Sun, Xue-Long,Tang, Jin-Shan
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p. 3359 - 3364
(2017/07/07)
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- USE OF CO2 FOR THE SYNTHESIS OF CYCLIC GLYCOCARBONATES AND LINEAR POLYGLYCOCARBONATES BY POLYCONDENSATION FROM GLYCANS
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Provided herein are methods for synthesizing cyclic carbonates, glycocarbonates, and polyglycocarbonates by reacting polyol glycans with carbon dioxide. Synthesis can include selective polycondensation of polyol glycan hydroxyl moieties.
- -
-
Paragraph 0063
(2016/11/02)
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- Benzylidene Acetal Protecting Group as Carboxylic Acid Surrogate: Synthesis of Functionalized Uronic Acids and Sugar Amino Acids
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Direct oxidation of the 4,6-O-benzylidene acetal protecting group to C-6 carboxylic acid has been developed that provides an easy access to a wide range of biologically important and synthetically challenging uronic acid and sugar amino acid derivatives in good yields. The RuCl3-NaIO4-mediated oxidative cleavage method eliminates protection and deprotection steps and the reaction takes place under mild conditions. The dual role of the benzylidene acetal, as a protecting group and source of carboxylic acid, was exploited in the efficient synthesis of six-carbon sialic acid analogues and disaccharides bearing uronic acids, including glycosaminoglycan analogues.
- Banerjee, Amit,Senthilkumar, Soundararasu,Baskaran, Sundarababu
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p. 902 - 906
(2016/01/16)
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- Compositions and methods for modification of biomolecules
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The present invention provides modified cycloalkyne compounds; and method of use of such compounds in modifying biomolecules. The present invention features a cycloaddition reaction that can be carried out under physiological conditions. In general, the invention involves reacting a modified cycloalkyne with an azide moiety on a target biomolecule, generating a covalently modified biomolecule. The selectivity of the reaction and its compatibility with aqueous environments provide for its application in vivo (e.g., on the cell surface or intracellularly) and in vitro (e.g., synthesis of peptides and other polymers, production of modified (e.g., labeled) amino acids).
- -
-
Page/Page column 53
(2016/03/12)
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- From d-glucuronic acid to l-iduronic acid derivatives via a radical tandem decarboxylation-cyclization
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A synthesis to l-iduronic derivatives, major components of heparin derived pentasaccharides was accomplished by formal inversion of configuration at C-5 of a d-glucuronic acid derivative through radical formation at C-5 using Barton decarboxylation followed by intramolecular radical addition on an acetylenic tether at O-4 giving exclusively a bicyclic sugar of l-ido configuration. Oxidation and ring opening of this bicyclic sugar led to a l-iduronate. This method opens the way to short syntheses of pentasaccharidic moiety of Idraparinux and congeners.
- Salamone, Stéphane,Boisbrun, Michel,Didierjean, Claude,Chapleur, Yves
-
-
- Probing the influence of a 4,6-O-acetal on the reactivity of galactopyranosyl donors: Verification of the disarming influence of the trans-gauche conformation of C5-C6 bonds
-
The effect of a 4,6-O-alkylidene acetal on the rate of acid-catalyzed hydrolysis of methyl galactopyranosides and of spontaneous hydrolysis of 2,4-dinitrophenyl galactopyranosides has been studied through the synthesis and hydrolysis of analogs in which O6 is replaced by a methoxymethylene unit in which the methoxy group adopts either an equatorial or an axial position according to the configuration. Consistent with earlier studies under both acid-catalyzed and spontaneous hydrolysis conditions, the alkylidene acetal, or its 7-carba analog, retards hydrolysis with respect to comparable systems lacking the cyclic protecting group. The configuration at C6 in the 7-carba analogs does not influence the rate of acid-catalyzed hydrolysis but has a minor influence on the rate of spontaneous hydrolysis of the 2,4-dinitrophenyl galactosides, confirming earlier studies on the role played by the hydroxymethyl group conformation on glycoside reactivity. The benzylidene acetal is found to stabilize the α-anomer of galactopyranose derivatives relative to monocyclic analogs. Reasons for the α-selectivity of 4,6-O-benzylidene- protected galactopyranosyl donors bearing neighboring group-active protecting groups at O2 are discussed.
- Moume-Pymbock, Myriame,Furukawa, Takayuki,Mondal, Sujit,Crich, David
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p. 14249 - 14255
(2013/10/21)
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- Polycarbonates derived from glucose via an organocatalytic approach
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An organocatalyzed ring-opening polymerization methodology was developed for the preparation of polycarbonates derived from glucose as a natural product starting material. The cyclic 4,6-carbonate monomer of glucose having the 1, 2, and 3 positions methyl-protected was prepared in three steps from a commercially available glucose derivative, and the structure was confirmed by means of NMR and IR spectroscopies, electrospray ionization mass spectrometry (MS), and single-crystal X-ray analysis. Polymerization of the monomer, initiated by 4-methylbenzyl alcohol in the presence of 1,5,7-triazabicyclo[4.4.0]dec-5-ene as the organocatalyst, proceeded effectively in a controlled fashion to afford the polycarbonate with a tunable degree of polymerization, narrow molecular weight distribution, and well-defined end groups, as confirmed by a combination of NMR spectroscopy, gel-permeation chromatography, and MALDI-TOF MS. A distribution of head-to-head, head-to-tail, and tail-to-tail regiochemistries was determined by NMR spectroscopy and tandem MS analysis by electron transfer dissociation. These polycarbonates are of interest as engineering materials because of their origination from renewable resources combined with their amorphous character and relatively high glass transition temperatures as determined by X-ray diffraction and differential scanning calorimetry studies.
- Mikami, Koichiro,Lonnecker, Alexander T.,Gustafson, Tiffany P.,Zinnel, Nathanael F.,Pai, Pei-Jing,Russell, David H.,Wooley, Karen L.
-
supporting information
p. 6826 - 6829
(2013/06/05)
-
- Poly(d-glucose carbonate) block copolymers: A platform for natural product-based nanomaterials with solvothermatic characteristics
-
A natural product-based polymer platform, having the characteristics of being derived from renewable materials and capable of breaking down, ultimately, into natural byproducts, has been prepared through the ring-opening polymerization (ROP) of a glucose-based bicyclic carbonate monomer. ROP was carried out via chain extension of a polyphosphoester (PPE) macroinitiator in the presence of 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) organocatalyst to afford the PPE-b-poly(d-glucose carbonate) (PDGC) block copolymer. This new copolymer represents a functional architecture that can be rapidly transformed through thiol-yne reactions along the PPE segment into a diverse variety of amphiphilic polymers, which interestingly display stimuli-sensitive phase behavior in the form of a lower critical solution temperature (LCST). Below the LCST, they undergo self-assembly to form spherical core-shell nanostructures that display a poorly defined core-shell morphology. It is expected that hydrophobic patches are exposed within the micellar corona, reminiscent of the surface complexity of proteins, making these materials of interest for triggered and reversible assembly disassembly processes.
- Gustafson, Tiffany P.,Lonnecker, Alexander T.,Heo, Gyu Seong,Zhang, Shiyi,Dove, Andrew P.,Wooley, Karen L.
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p. 3346 - 3353
(2013/09/24)
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- Process of preparation of L-iduronic acid comprising a decarboxylation/intramolecular cyclisation tandem reaction
-
The present invention relates to a process of preparation of L-iduronic acid and derivatives comprising a decarboxylation/intramolecular cyclisation tandem reaction. The present invention also relates to the intermediates of the process, as well as their use as intermediates in the preparation of Idraparinux.
- -
-
Paragraph 0133-0135
(2013/04/23)
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- PROCESS OF PREPARATION OF L-IDURONIC ACID AND DERIVATIVES COMPRISING A DECARBOXYLATION/INTRAMOLECULAR CYCLISATION TANDEM REACTION
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The present invention relates to a process of preparation of L-iduronic acid and derivatives comprising a decarboxylation/intramolecular cyclisation tandem reaction. The present invention also relates to the intermediates of the process, as well as their use as intermediates in the preparation of Idraparinux.
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-
- Hydroxy group acidities of partially protected glycopyranosides
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A comprehensive acidity study of carbohydrate hydroxy groups has been carried out. Relative acidities (Ke) were determined spectrophotometrically for partially methylated methyl α-D- glycopyranosides. Apparently, the acidity is strongly affected by intramolecular hydrogen bonding as well as stereochemistry and solvation. By comparison with pKe and pKa values of aliphatic alcohols and polyols the first estimation of the pKa values for partially protected glycopyranosides was obtained. These findings contribute to the understanding of the relative reactivities of carbohydrate hydroxy groups.
- Matwiejuk, Martin,Thiem, Joachim
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scheme or table
p. 2180 - 2187
(2012/06/30)
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- Access to new carbohydrate-functionalized polylactides via organocatalyzed ring-opening polymerization
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The 4-dimethylaminopyridine (DMAP) catalyzed ring-opening polymerization of lactide using various carbohydrate initiators has been assessed for the functionalization of polylactide. Selectively protected glucose derivatives bearing a free primary alcohol (Glc-1r) and a free secondary alcohol (Glc-2r), glucose and cyclodextrin diol derivatives (Glc-diol and CD-diol), methyl-α-d-glucopyranoside (Glc-Me) and native β-cyclodextrin (CD) were used as initiators. According to the solubility of the carbohydrate derivative, the polymerizations were conducted in chlorinated solvents and in the bulk. Relatively narrow distributions are obtained in high yields in the absence of side reactions, affording a 100% functionalization efficiency. The catalytic synthesis of new carbohydrate link-functionalized polylactides and carbohydrate core star polylactides is reported.
- Miao, Yong,Rousseau, Cyril,Mortreux, André,Martin, Patrick,Zinck, Philippe
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experimental part
p. 5018 - 5026
(2012/06/29)
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- Defining oxyanion reactivities in base-promoted glycosylations
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Saccharide oxyanions obtained by base treatment could be employed in glycosylation to give oligosaccharides with high stereo- and regioselectivities.
- Matwiejuk, Martin,Thiem, Joachim
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p. 8379 - 8381
(2011/09/14)
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- Synthesis of blockwise alkylated (1→4) linked trisaccharides as surfactants: Influence of configuration of anomeric position on their surface activities
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New carbohydrate-based surfactants consisting of hydrophilic cellobiosyl and hydrophobic glucosyl residues, methyl β-D-glucopyranosyl-(1→4)- α-D-glucopyranosyl-(1→4)-2,3,6-tri-O-methyl-α-D- glucopyranoside 1 (GβGαMα, G: glucopyranosyl residue, α and β: α-(1→4)- and β-(1→4) glycosidic bonds, M: methyl group), 2 (GβGβMα), 3 (GβGαMβ), 4 (G βGβMβ), 5 (G βGαEα, E: ethyl group), 6 (GβGβEα), 7 (G βGαEβ), 8 (G βGβEβ) and eight α-and β-glycoside mixtures (a mixture of 1 and 2: 1/2 = 62/38 (9), 32/68 (10); a mixture of 3 and 4: 3/4 = 69/31 (11), 32/68 (12); a mixture of 5 and 6: 5/6 = 62/38 (13), 33/67 (14); a mixture of 7 and 8: 7/8 = 59/41 (15), 29/71 (16)) were synthesized via combined methods consisting of acid-catalyzed alcoholysis of cellulose ethers and glycosylation of phenyl thio-cellobioside derivatives. Their surface activities in aqueous solution depended on their chemical structures: α- or β-(1→4) linkage between hydrophilic cellobiosyl and hydrophobic glucosyl blocks, methyl or ethyl groups of hydrophobic glucosyl block, and α- or β-linked ether group at the C-1 of hydrophobic glucosyl block. The mixing effect of α- and β-glycosides on surface activities was also investigated. As a result, ethyl β-D-glucopyranosyl-(1→4)-α-Dglucopyranosyl-(1→4)-2,3, 6-tri-O-ethyl-β-D-glucopyranoside 7 (GβG αEβ) had the highest surface activity, and its critical micellar concentration (CMC) and γCMC (surface tension at CMC) values of compound 7 were 0.5 mM(ca. 0.03 wt %) and 34.5 mN/m, respectively. The surface tensions of α- and β-glycoside mixtures except for compounds 9 and 10 were almost equal to those of pure compounds. The syntheses of the mixtures of α- and β-glycosides without purification process are easier than those of pure compounds. Thus, the mixtures should be more practical compounds for industrial use as a surfactant.
- Nakagawa, Atsushi,Kamitakahara, Hiroshi
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p. 1671 - 1683
(2011/11/12)
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- A hydrophilic azacyclooctyne for cu-free click chemistry
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(Chemical Equation Presented) Biomolecules labeled with azides can be detected through Cu-free click chemistry with cyclooctyne probes, but their intrinsic hydrophobicity can compromise bioavailability. Here, we report the synthesis and evaluation of a novel azacyclooctyne, 6,7-dimethoxyazacyclooct-4- yne (DIMAC). Generated in nine steps from a glucose analogue, DIMAC reacted with azide-labeled proteins and cells similarly to cyclooctynes. However, its superior polarity and water solubility reduced nonspecific binding, thereby improving the sensitivity of azide detection.
- Sletten, Ellen M.,Bertozzi, Carolyn R.
-
supporting information; experimental part
p. 3097 - 3099
(2009/04/18)
-
- Stereoselective mannich-like reactions of ester enolates generated on sugar templates: A novel access to a key intermediate for 1β-methylcarbapenem synthesis
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The Mannich-like reactions of the enolates generated from 2,3-di-O-protected 6-deoxy-4-O-propionyl-α-D-glucopyranosides with (3R,4R)-4-acetoxy-3-((R)-1-(t-butyldimethylsilyloxy)ethyl ]azetidin-2-one were investigated. The corresponding 2,3-di-O-methyl derivative provided the Mannich adduct in good to excellent stereoselectivity. From the major adduct, the azetidin-2-one incorporating an α-methyl acetic acid side chain at the C-4 position with ?-configuration was obtained by alkaline hydrolysis. This product, (3S,4S)-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl 1-4-1(R)-1-carboxyethylJazetidin-2-one, is a useful intermediate for the 1 ?-methylcarbapenem synthesis.
- Sasaki, Daisuke,Sawamoto, Daisuke,Takao, Ken-ichi,Tadano, Kin-ichi,Okue, Masayuki,Ajito, Keiichi
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p. 103 - 110
(2008/02/13)
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- Reconciling solvent effects on rotamer populations in carbohydrates - A joint MD and NMR analysis
-
The rotational preferences of the hydroxymethyl group in pyranosides is known to depend on the local environment, whether in solid, solution, or gas phase. By combining molecular dynamics (MD) simulations with NMR spectroscopy the rotational preferences for the ω angle in methyl 2,3-di-O-methyl- α-D-glucopyranoside (3) and methyl 2,3-di-O-methyl-α-D- galactopyranoside (6) in a variety of solvents, with polarities ranging from 80 to 2.3 D have been determined. The effects of solvent polarity on intramolecular hydrogen bonding have been identified and quantified. In water, the internal hydrogen bonding networks are disrupted by competition with hydrogen bonds to the solvent. When the internal hydrogen bonds are differentially disrupted, the rotamer populations associated with the ω angle may be altered. In the case of 3 in water, the preferential disruption of the interaction between HO6 and O4 destabilizes the tg rotamer, leading to the observed preference for gauche rotamers. Without the hydrogen bond enhancement offered by a low polarity environment, both 3 and 6 display rotamer populations that are consistent with expectations based on the minimization of repulsive intramolecular oxygen-oxygen interactions. In a low polarity environment, HO6 prefers to interact with O4, however, in water these interactions are markedly weakened, indicating that HO6 acts as a hydrogen bond donor to water.
- Gonzalez-Outeirino, Jorge,Kirschner, Karl N.,Thobhani, Smita,Woods, Robert J.
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p. 569 - 579
(2007/10/03)
-
- Analysis of the binding specificities of oligomannoside-binding proteins using methylated monosaccharides
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The binding specificities of the closely related lectins from Canavalia ensiformis and Dioclea grandiflora were examined using specifically O-alkylated mono- and disaccharides. Both lectins accept any substitution at the monosaccharide C2 hydroxyl group. The binding energy of C2-alkylated ligands-concanavalin A complexes increases by 1 kcal mol-1 for the C2-O-ethyl ligand, while the binding energies of the corresponding complexes with the Dioclea lectin are identical. Both lectins accept methyl, but not ethyl, substitution of the C3 hydroxyl, in contrast to earlier reports. The results are interpreted in terms of existing models of the concanavalin A binding site. While the results are consistent with a model of the concanavalin A extended binding site that places the non-reducing terminus of all disaccharides in the monosaccharide binding site, they point to the dangers of interpreting the binding behavior of unnatural saccharide ligands on the basis of crystallographic data obtained with native ligands.
- Chervenak, Mary C.,Toone, Eric J.
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p. 1963 - 1977
(2007/10/03)
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- Introduction of a chiral centre on C-6 of a carbohydrate unit: Application to the synthesis of the C-2 to C-15 fragment of ionomycin
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Glucose is converted into the α,β-unsaturated urono-8,4-lactone 29 using an intramolecular Wadsworth-Emmons reaction. Higher order cuprates add to the lactone to provide the C-6 substituted carbohydrate derivative with high stereoselectivity. This product can be converted into the dithiane 34b which when coupled with an appropriate epoxide yields compound 37 which contains the C-2 to C-15 fragment of ionomycin with the correct absolute stereochemistry at each asymmetric centre for conversion into ionomycin.
- Nicoll-Griffith,Weiler
-
p. 2733 - 2750
(2007/10/02)
-
- 2-PHENYL-1,3-BENZODITHIOLYLIUM TRIFLUOROMETHANESULFONATE: A REAGENT FOR THE CONVERSION OF ALCOHOLS INTO BENZYL ETHERS AND BENZOATES UNDER MILD CONDITIONS.
-
2-Phenyl-1,3-benzodithiolylium trifluoromethanesulfonate, easily prepared from 1,2-benzenedithiol, converts alcohols into dithioorthoesters and ultimately, benzyl ethers (Bu3SnH) and benzoates (HgO/HBF4).
- Mocerino, Mauro,Stick, Robert V.
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p. 3051 - 3054
(2007/10/02)
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- SYNTHESIS AND MASS SPECTRA OF 4-O-ACETYL-1,5-ANHYDRO-2,3,6-TRI-O-ETHYL-D-GLUCITOL AND THE POSITIONAL ISOMER OF 4-O-ACETYL-1,5-ANHYDRO-DI-O-ETHYL-O-METHYL-D-GLUCITOL AND 4-O-ACETYL-1,5-ANHYDRO-O-ETHYL-DI-O-METHYL-D-GLUCITOL
-
Reductive cleavage of fully methylated, partially O-ethylated cellulose or fully ethylated, partially O-methylated cellulose and subsequent acetylation had previously been shown to produce 4-O-acetyl-1,5-anhydro-2,3,6-tri-O-methyl-, -6-Oethyl-2,3-di-O-methyl-, -3-O-ethyl-2,6-di-O-methyl-, -2-O-ethyl-3,6-di-O-methyl-, -2,3,di-O-ethyl-6-O-methyl-, -2,6-di-O-ethyl-3-O-methyl-, -3,6-di-O-ethyl-2-O-methyl-, and -2,3,6-tri-O-ethyl-D-glucitol.Described herein is the independent synthesis of these derivatives, except for the first (which had been reported); and their (1)H-n.m.r. spectra, chemical-ionization (NH3) mass spectra, and electron-impact mass spectra are tabulated.
- Zeller, Samuel G.,D'Ambra, Anello J.,Rice, Michael J.,Gray, Gary R.
-
-
- Conformations of Epimers of Methyl 4,6-O-Benzylidene-2,3-di-O-Methyl-α-D-Glucopyranoside. An Example of Hindered Rotation of an Axial Phenyl Group as Observed by 13C Spin-Lattice Relaxation Times
-
The two epimeric 4,6-O-benzylidene derivatives of methyl 2,3-di-O-methyl-α-D-glucopyranoside were synthesised by base catalysed reaction with phenyldichloromethane.In one epimer the 1,3-dioxane ring has chair conformation with the phenyl ring in an equatorial orientation.Based on NMR arguments, the other epimer was also proved to have chair conformation with the phenyl group axially oriented.Comparison of the 13C shifts of the two epimers indicated a γ-gauche effect due to the axial phenyl.Moreover, spin-lattice relaxation time measurements revealed an ortho:para ratio of 3 for the equatorial epimer and a ratio close to unity for the axial epimer.This strongly indicates a fast rotation around the C-phenyl bond for the former and almost completely hindered rotation for the latter.Nuclear Overhauser effect measurements also support the two conformations.
- Svaan, Morten,Anthonsen, Thorleif
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p. 119 - 122
(2007/10/02)
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- ALKYLATION OF CARBOHYDRATES IN A CATALYTIC TWO-PHASE SYSTEM
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Alkylation of hydroxyl groups of sugars has been performed by means of primary alkyl halides or sulfates in a catalytic two-phase (CTP) system containing a concentrated, aqueous sodium hydroxide solution and a catalyst, i.e. tetra-n-butylammonium chloride.The corresponding ethers were formed with a very high yield.
- Szeja, Wieslaw
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p. 1503 - 1509
(2007/10/02)
-
- Further Stereoselective Reductions of 3-O-Hexafuranosyl S-Methyl Dithiocarbonates with Tributyltin Deuteride. A Comment on Mechanism
-
The reduction of 1,2:5,6-di-O-isopropylidene-3-O-(methylthio)thiocarbonyl-β-D-altrose, -mannose and -(3-2H)mannose with tributyltin deuteride and hydride leads to highly stereoselective syntheses of 3-deoxy-1,2:5,6-di-O-isopropylidene-β-D-(3-2H)altrose and -(3-2H)mannose.In addition, the reduction of a pair of diastereomeric dithiocarbonates with virtually no stereochemical constraints leads to the same diastereomeric mixture of reduced products, indicating a common radical intermediate for the reduction.
- Fuller, Trevor S.,Stick, Robert V.
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p. 2509 - 2515
(2007/10/02)
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