Showing papers on "Glucal published in 2017"
TL;DR: In this article, the synthesis of a bicyclic carbonate monomer of a d-glucal derivative, which originated from the natural product dglucose, in an efficient three-step procedure and its ring-opening polymerization (ROP), initiated by 4-methylbenzyl alcohol, via organocatalysis was demonstrated.
Abstract: Herein, we demonstrate the synthesis of a bicyclic carbonate monomer of a d-glucal derivative, which originated from the natural product d-glucose, in an efficient three-step procedure and its ring-opening polymerization (ROP), initiated by 4-methylbenzyl alcohol, via organocatalysis. The ROP behavior was studied as a function of time, catalyst type, and catalyst concentration by using size exclusion chromatography (SEC) and nuclear magnetic resonance (NMR) spectroscopy. Using a cocatalyst system of 1,8-diazabicyclo[5.4.0]undec-7-ene and 1-(3,5-bis(trifluoromethyl)phenyl)-3-cyclohexyl-2-thiourea (5 mol %) afforded poly(d-glucal-carbonate) (PGCC) with almost complete monomer conversion (ca. 99%) within 1 min, as analyzed by 1H NMR spectroscopy, and a monomodal SEC trace with dispersity of 1.13. The resulting PGCCs exhibited amorphous characteristics with a relatively high glass transition temperature at ca. 69 °C and onset decomposition temperature at ca. 190 °C, as analyzed by differential scanning calori...
32 citations
TL;DR: Er(OTf) 3 in 2-MeTHF provides a new and eco-friendly process for Ferrier glycosylation of sulfonamides and amino acids with various N -nucleophiles.
21 citations
TL;DR: A library of glucal-derived triazoles have been synthesized using the copper-catalyzed azide-alkyne cyclization reaction starting from 3,4,6-tri-O-acetyl-d-glucal.
8 citations
TL;DR: In this paper, a method for the preparation of 2-deoxy-d-glucose and purin-9-yl 2-Deoxy-α-d -glucopyranonucleosides was developed.
Abstract: Convenient and stereoselective methods for the preparation of 2-deoxy- d -glucose and purine 2-deoxy-α- d -glucopyranonucleosides were developed. Halogen-mediated O-glycosidation of d -glucal by bromine in MeOH followed by reductive removal of the halo group and hydrolysis of methoxy group by zinc in saturated aqueous sodium dihydrogen phosphate gave 2-deoxy- d -glucose. Treatment of 3,4,6-tri-O-acetyl- d -glucal with IBr and 2,6-dichloropurine based on haloetherification and subsequent reductive removal of iodine and deprotection allowed the isolation of purin-9-yl 2-deoxy-α- d -glucopyranonucleoside. Preparation of several purin-9-yl 2-deoxy-α- d -glucopyranoside derivatives is also reported. Their configuration was confirmed by single crystal X-ray analysis of the key intermediate 2,6-dichloro-9-(2-iodo-2-deoxy-α- d -glucopyranosyl)purine.
7 citations
TL;DR: By using Hf(OTf)4 as the catalyst, a series of 2,3-N- and C-unsaturated-glucosides have been synthesized from 3,4,6-tri-O-acetyl-d -glucal, 2, 4,6,tri- O-benzyl- d -GLucal and ((2R,3S)-3-acetoxy-2,3,dihydrofuran-2-yl)methyl acetate under mild reaction conditions in good yields with high
5 citations
TL;DR: In this paper, 2,3-Unsaturated C -(triazolyl) glycosyl acetates have been synthesized from 3,4,6-tri-O -acetyl-d -glucal using C -glycosylation and click chemistry and were then used in a palladium-catalyzed Tsuji-Trost type allylic azidation reaction to afford the corresponding regioisomeric glucal-azide derivatives.
Abstract: 2,3-Unsaturated C -(triazolyl)glycosyl acetates have been synthesized from 3,4,6-tri- O -acetyl- d -glucal using C -glycosylation and click chemistry and were then used in a palladium-catalyzed Tsuji–Trost type allylic azidation reaction to afford the corresponding regioisomeric glucal-azide derivatives. Copper-catalyzed azide-alkyne cycloaddition (CuAAC) reactions with these glucal-based allylic azides using CuI as the catalyst, led to the corresponding glucal-based bis(triazole) derivatives. Performing further functional group modification and another click (CuAAC) reaction with each of these bis(triazolyl) glycosyl derivatives afforded tris(triazolyl)glycosyl derivatives. Two libraries of regioisomeric bis(triazole) derivatives and a small library of regioisomeric tris(triazole) derivatives of glucal were then synthesized using different alkynes.
5 citations
TL;DR: A large difference in the N-terminal peptide sequence of both lipases resulted in a strong difference in catalytic properties between immobilized enzymes, with ROLpp being the most active, specific and regioselective heterogeneous biocatalyst in the hydrolysis of lactal hexaacetate.
3 citations
Patent•
31 May 2017
TL;DR: In this paper, a fungicide containing glucal and N,N-N-di-n-octyl diethylenetriamine acetate was described, and the total content of the effective components is 5.5-11.0%.
Abstract: The invention discloses a fungicide containing glucal and N,N-di-n-octyl diethylenetriamine acetate. The fungicide is characterized in that glucal and N,N-di-n-octyl diethylenetriamine acetate are used as effective components of the fungicide and are compounded according to a mass ratio of 1 to 10; the total content of the effective components is 5.5-11.0%. The fungicide has the beneficial effects that after the glucal and N,N-di-n-octyl diethylenetriamine acetate are reasonably compounded, the efficient, low-toxicity and safe fungicidal effect can be achieved, the rotten diseases of apple trees can be effectively prevented, the cost of independent application of biological pesticides can also be reduced, the consumption of chemical pesticides is reduced, the growth of crops is also promoted, the stress resistance of the crops is improved, and the generation of harmful cells in the crops is restrained.
18 Sep 2017