54522-57-5Relevant academic research and scientific papers
Regioselective Sulfonylation/Acylation of Carbohydrates Catalyzed by FeCl3 Combined with Benzoyltrifluoroacetone and Its Mechanism Study
Dong, Hai,Liu, Yu,Lv, Jian,Zhu, Jia-Jia
, p. 3307 - 3319 (2020/03/25)
A catalytic amount of FeCl3 combined with benzoyl trifluoroacetone (Hbtfa) (FeCl3/Hbtfa = 1/2) was used to catalyze sulfonylation/acylation of diols and polyols using diisopropylethylamine (DIPEA) or potassium carbonate (K2CO3) as a base. The catalytic system exhibited high catalytic activity, leading to excellent isolated yields of sulfonylation/acylation products with high regioselectivities. Mechanism studies indicated that FeCl3 initially formed [Fe(btfa)3] (btfa = benzoyl trifluoroacetonate) with twice the amount of Hbtfa under basic conditions in the solvent acetonitrile at room temperature. Then, Fe(btfa)3 and two hydroxyl groups of the substrates formed a five- or six-membered ring intermediate in the presence of the base. The subsequent reaction between the cyclic intermediate and a sulfonylation reagent led to the selective sulfonylation of the substrate. All key intermediates were captured in the high-resolution mass spectrometry assay, therefore demonstrating this mechanism for the first time.
Click chemistry route to tricyclic monosaccharide triazole hybrids: Design and synthesis of substituted hexahydro-4H-pyrano[2,3-f][1,2,3]triazolo[5,1-c][1,4]oxazepines
Konda, Saidulu,Rao, Pallavi,Oruganti, Srinivas
, p. 63962 - 63965 (2015/02/19)
A click chemistry approach to novel tricyclic monosaccharide triazole hybrids, namely, aryl substituted hexahydro-4H-pyrano[2,3-f][1,2,3]triazolo[5,1-c][1,4]oxazepine derivatives from an intramolecular 1,3-dipolar cycloaddition of 6-azido-4-O-propargyl glycopyranosides has been reported.
Application of the Synthetic Aminosugars for Glycodiversification: Synthesis and Antimicrobial Studies of Pyranmycin
Elchert, Bryan,Li, Jie,Wang, Jinhua,Hui, Yu,Rai, Ravi,Ptak, Roger,Ward, Priscilla,Takemoto, Jon Y.,Bensaci, Mekki,Chang, Cheng-Wei Tom
, p. 1513 - 1523 (2007/10/03)
A divergent approach was employed for the synthesis of aminosugars, from which a novel library of aminoglycoside antibiotics (pyranmycins) was synthesized. Pyranmycins have comparable antibacterial activity as neomycin, a clinically used aminoglycoside antibiotic, against Escherichia coli, Staphylococcus aureus, Bacillus subtilis, and Mycobacterium smegmatis. In addition, pyranmycins, like streptomycin, are bacteriocidal while isoniazid (INH) is bacteriostatic. Therefore, pyranmycins may provide new therapeutic options in the treatment against tuberculosis. Several members of pyranmycins also manifest modest anti-Tat and anti-Rev activities, which may aid in the development of new anti-HIV agents. Although the antibacterial activity of pyranmycins against aminoglycoside resistant bacteria is less than expected, the synthetic methodologies of utilizing a library of aminosugars can be a model for future studies of glycodiversification or glycorandomization.
Highly diastereoselective 1,4-addition of an organocuprate to methyl α-D-gluco-, α-D-manno-, or α-D-galactopyranosides tethering an α,β-unsaturated ester. Novel asymmetric access to β-C-substituted butanoic acids
Totani,Nagatsuka,Yamaguchi,Takao,Ohba,Tadano
, p. 5965 - 5975 (2007/10/03)
The 1,4-addition of magnesium divinylcuprate prepared from vinylmagnesium bromide and cuprous bromide to some 4-O-crotonyl derivatives of methyl α-D-glucopyranoside proceeds with a high level of diastereochemical induction, providing the adduct in good-to
Highly stereoselective 1,4-conjugate addition of organocopper reagents to methyl α-D-glucopyranoside derivatives tethering an unsaturated ester moiety at C-4 or C-6
Totani, Kiichiro,Nagatsuka, Takayuki,Takao, Ken-Ichi,Ohba, Shigeru,Tadano, Kin-Ichi
, p. 1447 - 1450 (2008/02/09)
(formula presented) The 1,4-conjugate additions of a variety of organocopper reagents to some 4-O-crotonyl derivatives of methyl α-D-glucopyranoside proceeded with a high level of diastereochemical induction to provide the adducts carrying a β-substituted
Total synthesis of (2S,3R,5S)-(-)-2,3-dihydroxytetradecan-5-olide, a new biologically active δ-lactone produced by Seiridium unicorne
Toshima, Hiroaki,Sato, Hiroji,Ichihara, Akitami
, p. 2581 - 2590 (2007/10/03)
The first total synthesis of (2S,3R,5S)-(-)-2,3-dihydroxytetradecan-5- olide (1), a new biologically active δ-lactone produced by Seiridium unicome, was accomplished from (R)-malic acid. In connection with the determination of the absolute configuration of 1, (2R,3S,5R)-(+)-2,3- dihydroxytetradecan-5-olide (ent-1) was also synthesized from D-glucose.
Isolation, structural determination, and total synthesis of a new biologically active δ-lactone produced by Seiridium unicorne
Toshima, Hiroaki,Watanabe, Ayako,Sato, Hiroji,Ichihara, Akitami
, p. 9223 - 9226 (2007/10/03)
The structure of a new biologically active δ-lactone, produced by Seiridium unicorne, was determined to be (2S,3R,5S)-(-)-2,3- dihydroxytetradecan-5-olide. The relative configuration was elucidated from NMR experiments. The synthesis of the enantiomer from D-glucose revealed the absolute configuration. The total synthesis of the natural form was also achieved from (R)-malic acid.
Synthesis of monosaccharide-fused azetidines
Michaud, Thierry,Chanet-Ray, Josette,Chou, Sithan,Gelas, Jacques
, p. 253 - 269 (2007/10/03)
Primary amines reacted upon 4,6-ditosylates of glucopyranosides to give an azetidine ring fused on C-4 and C-6 of the pyranose ring. On the other hand, the 4,6-ditosylate of benzyl mannopyranoside led to the 4,6-diamino-4,6-dideoxy derivative in a good yield. All the compounds and their precursors were identified by 1H and 13C NMR spectroscopy. Assignments of proton signals were made unambiguously using homodecoupling experiments.
Synthesis of novel amino acid glycoside conjugates
Heidelberg, Thorsten,Thiem, Joachim
, p. 145 - 153 (2007/10/03)
A new class of non-anomeric amino acid glycoconjugates can be prepared starting from either ω-amino- or ω-halodeoxyglucosides. Treatment of an ether-protected methyl 7-amino-6,7-dideoxy-α-D-glucoheptopyranoside with methyl aspartate isocyanate gave an urea-linked conjugate of methyl glucoheptopyranoside and aspartic acid. Nucleophilic displacement of the ether-protected methyl 6-chloro-6-deoxy-α-D-glucopyranoside with potassium succinimide followed by imide ring opening and amidation of the succinic acid monoamide with dimethyl iminodiacetate led to a conjugate of methyl 6-amino-6-deoxy-α-D-glucopyranoside and iminoodiacetate bridged by succinate.
Disaccharides to Inositol Saccharides: Synthesis of α-D-Galactopyranosyl-D-myo-inositol Derivatives from a Methyl 4-O-(α-D-Galactopyranosyl)-α-D-glucopyranoside Derivative
Mereyala, Hari Babu,Guntha, Sreenivasulu
, p. 841 - 844 (2007/10/02)
The disaccharide derivative 3 has been transformed into the galactopyranosylcyclohexanone derivative 5 by means of Ferrier carbocycle reaction of the enosaccharide 4.Compound 5 was converted into the enone 6 and then into the allylic alcohol 7.Oxidation o
