120693-82-5Relevant academic research and scientific papers
Conversion of D-xylose to protected D-lyxose derivatives and to D-lyxose, via the corresponding 1,2-anhydride
Popsavin, Velimir,Grabe?, Sanja,Stojanovi?, Biljana,Popsavin, Mirjana,Pejanovi?, Vjera,Miljkovi?, Du?an
, p. 110 - 115 (1999)
Acid hydrolysis of 3,5-di-O-benzyl-1,2-O-cyclohexylidene-α-D-xylofuranose gave the corresponding lactol, which was subsequently converted to the 3,5-di-O-benzyl-2-O-mesyl-D-xylofuranose. This compound readily reacted with sodium methoxide, sodium benzylate or sodium hydroxide (presumably via the corresponding 1,2-anhydride) to give the protected D-lyxofuranosides. These compounds were finally converted to methyl α-D-lyxopyranoside or to D-lyxose. Copyright (C) 1999 Elsevier Science Ltd.
Studies toward a synthesis of trilobatin B, a lignan from the liverwort Bazzania trilobata: Asymmetric construction of the tetrahydrofuran segment
Yoda, Hidemi,Nakaseko, Yuka,Takabe, Kunihiko
, p. 4217 - 4220 (2004)
A novel and stereocontrolled process is described for the asymmetric synthesis of the tetrahydrofuran segment of a 2,3-dicarboxy-6,7-dihydroxy-1- (3′,4′-dihydroxyphenyl)-1,2- dihydronaphthalene mono-ester, trilobatin B, a lignan from the liverwort Bazzani
Furanosyl Oxocarbenium Ion Conformational Energy Landscape Maps as a Tool to Study the Glycosylation Stereoselectivity of 2-Azidofuranoses, 2-Fluorofuranoses and Methyl Furanosyl Uronates
van der Vorm, Stefan,Hansen, Thomas,van Rijssel, Erwin R.,Dekkers, Rolf,Madern, Jerre M.,Overkleeft, Herman S.,Filippov, Dmitri V.,van der Marel, Gijsbert A.,Codée, Jeroen D. C.
supporting information, (2019/04/30)
The 3D shape of glycosyl oxocarbenium ions determines their stability and reactivity and the stereochemical course of SN1 reactions taking place on these reactive intermediates is dictated by the conformation of these species. The nature and co
PROCESSES FOR PREPARING 2-DIHALO RIBOLACTONES
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Page/Page column 73; 75, (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.
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
Diastereoselective concise syntheses of the polyhydroxylated alkaloids DMDP and DAB
Bouillon, Marc E.,Pyne, Stephen G.
, p. 475 - 478 (2014/01/06)
A diastereoselective concise synthesis of the iminosugars DMDP and DAB is presented starting from l-xylose and affording the two alkaloids in good yields of 35% and 22% over seven and eight steps, respectively. The Petasis borono-Mannich reaction of 3,5-di-O-benzyl-l-xylofuranose with benzylamine and (E)-styrylboronic acid served as the nitrogen-introducing key step furnishing the new C-N bond in an entirely diastereoselective manner. A chemo- and regioselective O-mesylation followed by an intramolecular SN2- cyclisation allowed the formation of the pyrrolidine ring. Ozonolysis of the styryl double bond and subsequent reduction to form the C-5 hydroxymethyl substituent followed by hydrogenolysis of the benzyl protecting groups concluded the DMDP synthesis. Furthermore, an unexpected fragmentation process during the ozonolysis reaction also gave access to the C-5 decarbinolated DMDP derivative DAB.
1,2-Cyclic sulfite and sulfate furanoside diesters: improved syntheses and stability
Hardacre, Christopher,Messina, Ivano,Migaud, Marie E.,Ness, Kerry A.,Norman, Sarah E.
experimental part, p. 6341 - 6347 (2009/12/04)
The facile syntheses of 1,2- and 3,5-cyclic sulfite and sulfate furanoside diesters were conducted in molecular solvents and ionic liquids in the presence of immobilised morpholine. Molecular solvents and ionic liquids performed similarly with regards to overall yields. However, the use of ILs allowed for the reactions to be carried out under atmospheric conditions and showed good recyclability. Additionally, increases in product stability was achieved in ILs over organic solvents, in particular, in bis{(trifluoromethanesulfonyl)imide} and trispentafluoro-ethyltrifluorophosphate-based ionic liquids, which were also excellent media to control the hydrolysis of thionyl chloride and sulfuryl chloride.
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
Oxetane δ-amino acids: Chemoenzymatic synthesis of 2,4-anhydro-5-N-(t-butoxycarbonyl)amino-D-lyxonic acid
Dias Lucas, Susana,Iding, Hans,Alker, Andre,Peter Wessel, Hans,Pilar Rauter, Amelia
, p. 187 - 196 (2007/10/03)
Starting from 1,2-O-isopropylidene-D-xylose, methyl 2,4-anhydro-3,5-di-O- benzyl-D-lyxonate (4) was synthesized. Debenzylation and transformation of the primary hydroxyl group yielded methyl 2,4-anhydro-5- N-(t-butoxycarbonyl)amino- D-lyxonate (9). While
Simple entry into isonucleosides: Synthesis of 6-amino-9-[(3S,4S,5R)-4- hydroxy-5-(hydroxymethyl)tetrahydrofuran-3-yl]purine
Mereyala, Hari Babu,Mamidyala, Sreeman Kumar
, p. 2965 - 2966 (2007/10/03)
A simple and efficient method for the preparation of isonucleoside 7 is described. The preparation of 1,4-anhydroxylitol 4, a key intermediate, is described by intramolecular cyclization of (2S,3R,4R)-3,5-dibenzyloxypentan-1,2, 4-triol 3 using diethyl car
