41341-99-5Relevant academic research and scientific papers
Xylonucleic acid: Synthesis, structure, and orthogonal pairing properties
Maiti, Mohitosh,Maiti, Munmun,Knies, Christine,Dumbre, Shrinivas,Lescrinier, Eveline,Rosemeyer, Helmut,Ceulemans, Arnout,Herdewijn, Piet
, p. 7189 - 7200 (2015)
There is a common interest for studying xeno-nucleic acid systems in the fields of synthetic biology and the origin of life, in particular, those with an engineered backbone and possessing novel properties. Along this line, we have investigated xylonuclei
PROCESSES FOR PREPARING 2-DIHALO RIBOLACTONES
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, (2017/06/21)
Methods for forming 2-bromo, 2-fluoro ribofuranose intermediates and 2-chloro, 2- fluoro ribofuranose intermediates for use in preparing antiviral nucleosides are disclosed. Methods for forming nucleosides, and nucleoside prodrugs, using the intermediates, are also disclosed. The methods all produce intermediates, and the resulting nucleosides and prodrugs thereof, wherein the chirality of the carbon at the 2-position is controlled. In some embodiments, the chemistry involves using chiral auxiliaries, such as (R)-2,2-dimethyl-l,3- dioxolane-4-carbaldehyde, and in other embodiments, the chemistry involves using chiral starting materials, such as D-xylose.
Methanesulfonic-acid-catalysed ring opening and glycosylation of 1,2-(Acetylcyclopropane)-annulated d -lyxofuranose
Wang, Cong,Ma, Xiaofeng,Zhang, Jichao,Tang, Qin,Jiao, Wei,Shao, Huawu
, p. 4592 - 4599 (2014/08/05)
A mild and effective method for the synthesis of 2-C-branched disaccharides, glycoconjugates, and nucleoside analogues is described. 1,2-(acetylcyclopropane)-annulated D-lyxofuranose underwent ring opening catalysed by CH3SO3H to act as an efficient glycosyl donor and give the glycosylation products in good yields and with high diastereoselectivities. Copyright
Synthesis of purine nucleosides from D -glucuronic acid derivatives and evaluation of their cholinesterase-inhibitory activities
Xavier, Nuno M.,Schwarz, Stefan,Vaz, Pedro D.,Csuk, Rene,Rauter, Amelia P.
, p. 2770 - 2779 (2014/05/06)
Glucuronolactones were used as precursors for N9 and N 7 purine nucleosides containing glucuronic acid derivatives in their structures. Acetylated N-benzylglucofuran- and glucopyranuronamides were synthesized in a few steps from glucofuranurono-6,3-lactone. They were converted into the corresponding furanosyl and pyranosyl uronamide-based nucleosides by N-glycosylation with silylated 2-acetamido-6-chloropurine in the presence of trimethylsilyl triflate. The triacetylated bicyclic lactone was coupled itself with the nucleobase to give bicyclic N9,N7 nucleosides. Tri-O-acetylglucopyranurono-6,1-lactone was used for the first time as a glycosyl donor for N-glycosylation, and led to β-configured N9- and N7-linked purinylglucuronides under reaction conditions similar to those used with the 1-O-acetyl-substituted glycosyl donors. The cholinesterase inhibitory profiles of the synthetic nucleosides bearing glucuronic acid derivatives as glycons were evaluated, and they showed moderate selective acetylcholinesterase inhibitory activities (Ki = 14.78-50.53 μM). The best inhibition was shown by the furanosyl N 9-linked uronamide-based purine nucleoside. The synthesis of furanosyl and pyranosyl N9 and N7 purine nucleosides containing glucofuranurono-6,3-lactone, N-benzylglucuronamide, and glucuronic acid moieties is reported. Glucuronolactones were used as glycosyl donors or converted into suitable 1-O-acetyl derivatives for purine glycosylation. Some nucleosides showed moderate and selective inhibition of acetylcholinesterase. Copyright
Straightforward and highly diastereoselective synthesis of 2,2-di-substituted perhydrofuro[2,3-b]pyran (and furan) derivatives promoted by BiCl3
Ma, Xiaofeng,Tang, Qin,Ke, Jun,Zhang, Jichao,Wang, Cong,Wang, Haibo,Li, Yuxue,Shao, Huawu
supporting information, p. 7085 - 7087 (2013/09/02)
An effective and facile method for the synthesis of 2,2-di-substituted perhydrofuro[2,3-b]pyran (and furan) derivatives is described. The cyclization of 1,2-cyclopropanated sugars with olefins in the presence of BiCl3 is highly diastereoselecti
InCl3 catalyzed highly diastereoselective [3 + 2] cycloaddition of 1,2-cyclopropanated sugars with aldehydes: A straightforward synthesis of persubstituted bis -tetrahydrofurans and perhydrofuro[2,3- b ]pyrans
Ma, Xiaofeng,Tang, Qin,Ke, Jun,Yang, Xinglong,Zhang, Jichao,Shao, Huawu
, p. 5170 - 5173 (2013/11/06)
A mild and efficient strategy for the construction of persubstituted bis-tetrahydrofuran and perhydrofuro[2,3-b]pyran derivatives has been developed. Persubstituted cyclization products were obtained in good to excellent yields. The [3 + 2] cycloaddition of 1,2-cyclopropanated sugars with aldehydes in the presence of InCl3 is highly diastereoselective.
Design and synthesis of carbohydrate based medium sized sulfur containing benzannulated macrocycles: Applications of Sonogashira and Heck coupling
Hussain, Altaf,Yousuf, Syed Khalid,Sharma, Deepak K.,Mallikharjuna Rao,Singh, Baldev,Mukherjee, Debaraj
supporting information, p. 5517 - 5524 (2013/07/05)
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
C1-symmetric diphosphite ligands derived from carbohydrates: Influence of structural modifications on the rhodium-catalyzed asymmetric hydroformylation of styrene
Gual, Aitor,Godard, Cyril,Claver, Carmen,Castillon, Sergio
experimental part, p. 1191 - 1201 (2009/07/11)
New 3,5-diphosphite-substituted xylofuranoside (1b, 25a,b, and 26a,b) and glucofuranoside (3a, 7a, 8a,b) ligands with C1 symmetry have been prepared and used in the Rh-catalyzed asymmetric hydroformylation of styrene. The main structural features of these ligands are a) the presence of a 6-O-isopropyl group in ligands with a gluco configuration, b) the absence of 1,2-O-isopropylidene, a common group in many ligands with a furanoside skeleton, c) the presence of an alkyl chain bound to the 2-OH, and d) modification of the diol in the phosphite moiety. Modification of the carbohydrate backbone and diphosphite bridge affects the activity and selectivity of the reaction. Catalytic systems with ligands 1b and 8b were not active at 40 °C, although the formation of the expected hydride species [RhH(CO)2(1b)] was demonstrated by NMR spectroscopy. The highest enantioselectivity (83%) was obtained with the catalytic system Rh/8a. The complex [RhH(CO)2(8a)] was characterized by NMR spectroscopy using high-pressure techniques and was shown to exist in solution as two isomers in equilibrium; the two isomers adopt an equatorial-equatorial (eq-eq) configuration. Wiley-VCH Verlag GmbH & Co. KGaA, 2009.
Stereoselective 1,4-phenyl migration from silicon to carbon in α-siloxy cyclic acetal systems: A concise synthesis of 1,2-cis-phenyl C-glycoside and enantioenriched silanol
Nakazaki, Atsuo,Usuki, Junji,Tomooka, Katsuhiko
experimental part, p. 2064 - 2068 (2009/05/07)
The treatment of O-glycoside with alcohol in the presence of montmorillonite K10 clay and 4-? MS yields the 1,4-aryl migration product with a 1,2-cis-phenyl C-glycoside scaffold and a chiral silyl moiety with high stereoselectivity.
Novel D-xylose derivatives stimulate muscle glucose uptake by activating AMP-activated protein kinase α
Gruzman, Arie,Shamni, Ofer,Yakir, Moriya Ben,Sandovski, Daphna,Elgart, Anna,Alpert, Evgenia,Cohen, Guy,Hoffman, Amnon,Katzhendler, Yehoshua,Cerasi, Erol,Sasson, Shlomo
body text, p. 8096 - 8108 (2009/12/07)
Type 2 diabetes mellitus has reached epidemic proportions; therefore, the search for novel antihyperglycemic drugs is intense. We have discovered that D-xylose increases the rate of glucose transport in a non-insulin-dependent manner in rat and human myot
