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1.
The IDCP-promoted intramolecular C-glycosylation of pentenyl α-mannopyranosides carrying, at O-2, an activated benzyl group gave, unexpectedly, the 1,2-trans-fused bicyclic product which corresponds to an α-C-aryl mannopyranose derivative. This remarkable, strained C-glycosyl compound was rapidly epimerized to the more stable 1,2-cis product on treatment with BF3·Et2O. The IDCP-reaction product could be elaborated into a 2-(α-C-mannopyranosyl)-3,4,5-trimethoxybenzyl alcohol derivative. 相似文献
2.
2-(Per-O-acetyl-β-d-glycopyranosyl)-1,4-dimethoxybenzenes led to C-glycosyl-hydroquinones suitable for preparing C-glycosylated analogs of vitamin E, having the sugar moiety free or acetylated. 相似文献
3.
Xianghui Wen 《Tetrahedron letters》2004,45(8):1773-1775
Diethyl C-(2-deoxy-2-acetamido-β-d-mannopyranosyl)methylphosphonate and dimethyl C-(2-deoxy-2-acetamido-β-d-glucopyranosyl)methylphosphonate were stereoselectively prepared from N-acetyl d-glucosamine. Routes to such compounds starting from d-GlcNAc have been problematic, but we have found short and efficient implementations of this highly desirable transformation. 相似文献
4.
Tashfeen Aslam 《Tetrahedron letters》2005,46(18):3249-3252
Two C-glycosides related to the recurrent α-d-arabinofuranosyl-(1→5)-α-d-arabinofuranosyl structural motif of mycobacterial arabinan have been prepared by routes involving acetylenic intermediates. 相似文献
5.
Ugo Chiacchio Filippo Genovese Vito Librando Antonio Rescifina Antonio Procopio 《Tetrahedron》2004,60(2):441-448
A new class of homo-N,O-nucleosides has been designed, based on the 1,3-dipolar cycloaddition of C-substituted nitrones with allyl nucleobases. The N-methyl-C-ethoxycarbonyl nitrone 1, and the C-α-silyloxymethyl-N-methyl nitrone 7 have been exploited: the stereochemical features of the obtained nucleosides are dependent on the nature of the dipole. The results obtained with DFT calculations fully agree with the experimental results and successfully reproduce the experimentally observed reversal of endo/exo selectivity for nitrones 1 and 7. 相似文献
6.
Jing-Jing Zhu Chao-Feng Zhang Mian Zhang S.W. Annie Bligh Li Yang Zhi-Min Wang Zheng-Tao Wang 《Journal of chromatography. A》2010,1217(33):5384-5388
Six C-glucosyl anthrones were characterized as three pairs of epimers by on-line high performance liquid chromatography–circular dichroism (HPLC–CD) analysis and isolated from the roots of Rumex dentatus by column chromatography. Their structures were elucidated by mass spectrometry, nuclear magnetic spectroscopy and HPLC–CD analysis. They are 10R-C-β-d-glucosyl-10-hydroxyemodin-9-anthrone (rumejaposide E, 1) and 10S-C-β-d-glucosyl-10-hydroxyemodin-9-anthrone (rumejaposide F, 2), 10R-C-β-d-glucosylemodin-9-anthrone (rumejaposide G, 3) and 10S-C-β-d-glucosylemodin-9-anthrone (rumejaposide H, 4), 10S-C-β-d-glucosyl-10-hydroxychrysophanol-9-anthrone (cassialoin, 5) and 10R-C-β-d-glucosyl-10-hydroxychrysophanol-9-anthrone (rumejaposide I, 6). Rumejaposides F–I (2–4 and 6) were new C-glucosyl anthrones. Rumejaposide E (1) and cassialoin (5) were isolated for the first time in Rumex plants. On-line HPLC–UV–CD analysis was a useful tool for structure elucidating epimeric C-glycosides anthrones 3–6 because of the poor stability of the pure isomers (3 and 4) and the minute quantity of 5 and 6 in the mixture. 相似文献
7.
Norio SaitoFumi Tatsuzawa Kazumitsu MiyoshiAtsushi Shigihara Toshio Honda 《Tetrahedron letters》2003,44(36):6821-6823
A novel C-glycosylanthocyanin was isolated from the flowers of Tricyrtis formosana cultivar Fujimusume, and its structure was elucidated to be 8-C-β-d-glucopyranosylcyanidin 3-O-(6-O-malonyl)-β-d-glucopyranoside by chemical and spectroscopic methods. 相似文献
8.
Éva Bokor Attila Fekete Gergely Varga Béla Szőcs Katalin Czifrák István Komáromi László Somsák 《Tetrahedron》2013
Synthesis of O-perbenzoylated 3-(β-d-glucopyranosyl)-5-substituted-1,2,4-triazoles, precursors of potent inhibitors of glycogen phosphorylase, was studied by ring closures of N1-acyl-carboxamidrazone type intermediates. Reactions of C-(β-d-glucopyranosyl)formimidate or C-(β-d-glucopyranosyl)formamidine with acid hydrazides as well as acylation of C-(β-d-glucopyranosyl)formamidrazone by acid chlorides unexpectedly gave the corresponding 1,3,4-oxadiazoles instead of 1,2,4-triazoles. The desired triazoles were obtained in reactions of C-(β-d-glucopyranosyl)formamidine or C-(β-d-glucopyranosyl)formyl chloride with arenecarboxamidrazones, and also in acylations of N1-tosyl-C-(β-d-glucopyranosyl)formamidrazone with acid chlorides. Theoretical calculations (B3LYP and M06-2X DFT with the standard 6-31G(d,p) basis set) on simple model compounds with methyl and phenyl substituents to understand the bifurcation of the ring closure of N1-acyl-carboxamidrazones indicated that in general the reaction led to 1,2,4-triazoles. However, the probability of the 1,3,4-oxadiazole forming pathway was shown to be significantly higher with N1-benzoyl-acetamidrazones, which were closest analogues of the intermediates resulting in C-glucosyl-1,3,4-oxadiazoles. It was thereby demonstrated that the substitution pattern of the N1-acyl-carboxamidrazones played a fundamental role in determining the direction of the ring closing reaction. 相似文献
9.
Takumi Furuta 《Tetrahedron》2004,60(42):9375-9379
The total synthesis of anti-inflammatory active flavone C-glycoside isolated from oolong tea extract is achieved. Introducing a C-glucosyl moiety to an aryl system and constructing a fused tetracyclic ring characteristic to this natural product were conducted based on the O-to-C rearrangement of sugar moiety and the successive intramolecular Mitsunobu reaction, respectively. This concise and efficient synthetic pathway is applicable to the large-scale synthesis of target flavone and for constructing a large library of related compounds. 相似文献
10.
Malati Raghunath 《Tetrahedron letters》2005,46(47):8213-8216
Among the bisphosphine ligands, we have previously developed Cn-TunePhos (n = 1-6) as a family of ligands with tunable bite angles. The increase in spacer -CH2- groups in this family of ligands causes changes in ligand dihedral angle, which in turn causes P-Pd-P bite angle variation. Pd-catalyzed asymmetric alkylations and cycloadditions have been tested with Cn-TunePhos ligands. This study aims at a possible correlation between ligand bite angles with enantioselectivity of the Pd-catalyzed asymmetric products. 相似文献
11.
Stereoselective synthesis of 3-α-C-glucosides of d- and l-fagomine from the corresponding C-disaccharides is reported. The ethyl glycoside of perbenzylated C-disaccharide 8 was converted via the corresponding thioglycoside 10 and reducing C-disaccharide 11, into substituted alditol 12 which, upon oxidation and double reductive amination stereoselectively afforded pure perbenzylated d-fagomine C-glucoside 14. In the same manner, the ethyl glycoside of perbenzylated C-disaccharide 9 was stereoselectively converted into perbenzylated l-fagomine C-glucoside 15. 相似文献
12.
One pot synthesis of the butenonyl-C-β-d-glycosides with malononitrile in the presence of K2CO3 in water under mild and green reaction conditions leading to the formation of small library of multifunctional biphenyl methyl-C-β-d-glycosides in good yields has been reported. The reaction is equally applicable with the substrates having different glycosyl pyranoses and aromatic rings with different substituents. 相似文献
13.
2-Cyanopyridazin-3(2H)-ones are novel, effective, selective and electrophilic cyanating agents. A variety of amino, thiol and carbon nucleophiles are chemoselectively N-, S- or C-cyanated in excellent yield using 2-cyanopyridanzin-3(2H)-ones in water or tetrahydrofuran. 相似文献
14.
The diffraction peak broadening induced by hydrogen absorption-desorption cycling has been analyzed in four different Laves phase compounds with the C14 and C15 structures. The broadening is due to strain most probably originating from dislocations generated at the interface between the α and β hydride phases in connection with the cell volume difference between the two phases. It has been shown that it is strongly compound dependent. In the case of the C14 structure, the broadening is large and isotropic, and the latter can be related to the isotropy of the elastic constants of the metallic phase. The broadening is less for the compounds with the C15 structure, which can be related to a possibly softer lattice. Better ageing properties after long-term cycling are predicted for this crystal structure. 相似文献
15.
Anatoliy Marchenko Georgyi KoidanAnastasiya Hurieva Aleksandr SavateevAleksandr Kostyuk 《Tetrahedron letters》2013
A direct synthetic approach to C-phosphanyl-N,N-dialkyl-N′-aryl(alkyl)-formamidines was developed. It was shown that phosphorylation of the formamidines proceeds at the nitrogen atom affording N-phosphanylformamidinium salts. Upon deprotonation, these salts gave C-phosphanylformamidines via formation of carbenes followed by a 1,2-phosphorus shift. 相似文献
16.
Stephen HanessianRoger Machaalani 《Tetrahedron letters》2003,44(45):8321-8323
A five-step practical and stereocontrolled synthesis of α- and β-pseudouridines from d-ribonolactone is described. The key step involves a highly stereoselective reduction of a hemiketal C-nucleoside intermediate in each case. Multi-gram quantities of β-pseudouridine can now be made available. 相似文献
17.
Intramolecular metal-catalyzed amination of a pseudo-anomeric C-H bond in a C-glycoside is reported. Treatment of α,β-C-carbamoyloxymethyl- or β-C-sulfamoyloxymethyl glycosides with Rh2(OAc)4, PhI(OAc)2, and MgO provided original spirooxazolidines or spirooxathiazolidines in reasonable yields. No correlation between ‘anomeric’ stereochemistry and insertion efficiency was found for the conversion of carbamate derivatives whereas amination reactions of the corresponding sulfamate esters were found to be strongly dependent on the anomeric configuration. 相似文献
18.
Anatoliy Marchenko 《Tetrahedron》2010,66(21):3668-7758
C-Phosphorylated (PV) arylformamidines have been prepared by the reaction of N-arylamidotrichloromethyl derivatives of phosphorus, thiophosphorus, and selenophosphorus acids with secondary amines. Dependence of the reaction on the nature of chalcogene, electronic and steric factors has been studied. By reduction of N-arylformamidinophosphonoselenides the corresponding C-phosphorylated (PIII) arylformamidines have been synthesized. 相似文献
19.
Teresa M.V.D. Pinho e Melo Maria I.L. Soares Hamish McNab 《Tetrahedron letters》2004,45(20):3889-3893
Extrusion of sulfur dioxide from pyrrolo[1,2-c]thiazole-2,2-dioxides led to the synthesis of functionalised pyrroles via the generation of 1-azafulvenium methides. Sealed tube reaction conditions allowed the synthesis of N- and C-vinylpyrroles whereas from FVP methyl 1,3-dimethyl-5-oxo-5H-pyrrolizine-2-carboxylate and 4-oxo-1,4-dihydro-1-aza-benzo[f]azulene-3-carboxylates were obtained. These last compounds could also be obtained from the FVP of the N- and C-vinylpyrroles. 相似文献
20.
2′-Carbonyl 5-S-acetyl-C-glycofuranosides and 2′-carbonyl 4-S-acetyl-C-glycopyranosides were converted in good yields to respective 5-thio-C-glycopyranosides and 4-thio-C-glycofuranosides under base treatment. The transformation was resulted from β-elimination on 2′-carbonyl C-glycoside to form α,β-conjugated aldehyde (or ketone) and following intramolecular hetero-Michael addition by the thiol group. 相似文献