Showing papers in "Journal of Carbohydrate Chemistry in 2007"

TL;DR: Highly α‐selective sialylation of sialic acid N‐phenyltrifluoroacetimidate with various galactose and lactose acceptors has been achieved by introducing the C‐5 N‐phthalyl group on the donor, which is amenable to large‐scale synthesis.

TL;DR: In this article, a reagent mixture of ammonium iodide, hydrogen peroxide, and acetic anhydride/acetic acid in acetonitrile was used to convert protected glycals and α-1,2-cyclopropanated sugars.

TL;DR: In this article, the synthesis of new benzylidene-protected glucosyl and mannosyl methyl 3,5-dinitrosalicylate (DISAL) donors, their application in O−glycosylations, and comparison with a torsionally “disarmed” donors, were performed in the absence of strong Lewis acids, but in the presence of lithium perchlorate or triflate, using either conventional heating to 40 to 60°C or precise microwave heating to 100 to 150°C.

TL;DR: In this article, the aqueous solution equilibration of dglucaric acid with its lactone forms was studied by NMR with and without acid catalysis.

TL;DR: In this article, the coupling reaction of 3,4,6,tri-O'acetyl, O 'acetyl-acetyl−α−d−glucopyranoside 2−O'lactone 1 (α−CMGL) with two kinds of lipophilic amines, aminosteroids and fatty amines was shown to yield the corresponding free αglucolipid amides.

TL;DR: The 1,3-dipolar cycloaddition of unsaturated D−threo−hexaldonolactone 3 and a six-membered cyclic nitrone 11 led to a single adduct, which could be transformed into (1S, 2S, 3S, 9aS)−2,3−dihydroxy−1−hydroxymethyl−quinolizidine 28 related to epilupinine via a reaction sequence involving rearrangement of the six−membered lactone ring into a five-mem

TL;DR: In an attempt to find competitive inhibitors of the trans‐sialidase of the pathogen Trypanosoma cruzi, conjugates of carbocyclic sialylmimetics and galactose derivatives are synthesized and an interesting preference for ethylidene‐spacered conjugate involving the 3‐position of the sugar is revealed.

TL;DR: In this paper, microwave assisted organic synthesis (MAOS) has been used to accelerate the conversion of Lascorbic acid (1) and Discorbic acids (2) to the title heterocycles by conversion to 3.

TL;DR: In this paper, a mass spectrometric study of oligosaccharides consisting of the core moiety with one O-polysaccharide repeating unit attached, which were derived from the SR-form LPSs of Providencia strains of various O-serogroups, was performed.

TL;DR: In this article, a trifluoromethanesulfonate-catalyzed solvent-free per-O-acetylation with stoichiometric acetic anhydride proceeds in high yield to afford exclusively pyranose products as anomeric mixtures.

TL;DR: In this paper, the crystal structure analysis of N−(1−deoxy−β−D−fructopyranos−1−yl)−L−proline monohydrate is presented.

TL;DR: It was found that these 1‐thioglycosides were excellent glycosyl donors, and especially 2‐thio‐sialoside prepared from 1 and 2 afforded the best result to date in terms of α‐ and β‐selectivity in the sialylation where only the single C‐3 hydroxyl group of acceptor D‐galactopyranoside was free.

TL;DR: In this article, the transformation of 1−O−unprotected glucose and galactose derivatives into O−glycosyl dichloro−cyanoacetimidates (2a−d) was performed with DBU as base.

TL;DR: The structure of these new Oβ-Dglucosides was established on the basis of chemical, elemental, and spectral analysis as discussed by the authors, and these compounds were evaluated for their in vitro biological activity.

TL;DR: A convenient microwave‐mediated condensation of D‐gluconic acid with o‐phenylenediamines provided the respective acyclonucleoside benzimidazole in short time and good yield.

TL;DR: Ellman's dihydropyran resin was used for selective protection of monosaccharide thioglycosides and glycosides following on‐resin acylation and subsequent cleavage of the polymer‐bound intermediates.

TL;DR: The partial sequence of the betaglycan composed of the tetraosyl hexapeptide, which was directly usable as a probe for enzymatic glycosyl transfer, is synthesized for the first time.

TL;DR: In this paper, 3,5,diazido, 3, 5,dideoxy, and 2,3,5 trideoxyfuranoses with ribo-and xylo-configuration were prepared using different approaches.

TL;DR: In this article, the synthesis of the aliphatic subunit 9 of the macrolide LL•Z1640•2 (I), starting from a 4−deoxy−D•mannose derivative 2a, is described.

TL;DR: The results about the solubility and swelling index data of hydrogels showed that their use as models of drug delivery is technically feasible.

TL;DR: The microwave assisted organic synthesis (MAOS) has proven to be practical to provide heterocycles from sugar osazones; an efficient method was developed for the characterization of sugars via their osazone 1, 4 using microwave irradiation.

TL;DR: The synthesis of a novel carbasugar amino acid (15), starting from D‐glucose and using the Ferrier rearrangement as a key step, is reported.

TL;DR: A general, odorless, one‐pot methodology has been developed for the preparation of 1,2‐trans‐thioglycosides and thio‐Michael addition products of carbohydrate derivatives through triphenyl phosphine‐mediated cleavage of disulfides and reaction of the thiolate formed in situ with glycosyl bromides and glycosol conjugated alkenes.

TL;DR: In this article, a triester triester, Dibutyl 3,4,di,Obenzyl 6,6,O•(fluorenylmethoxycarbonyl)•2•O•pivaloyl•β•D•glucopyranoside phosphate, not accessible by other methods, was prepared this way.

TL;DR: In this article, caged intramolecular ketals of β-C-glycosidic ketones were obtained from pyranoses, and the structures of the new compounds were elucidated by NMR and HRMS spectral analysis.

TL;DR: surface tension measurements showed up the surface activity of both compounds, while enzyme inhibition assays indicated that 9 could inhibit bovine β‐N‐acetylglucosaminidase but not Serratia marcescens chitobiase nor hen egg‐white lysozyme.

TL;DR: In this paper, the Corey-Seebach method was applied to dglucosamine propane and dithioacetal derivatives, yielding Nphthaloyl, N-Boc, and N-Ac derivatives.

TL;DR: In this paper, a Wittig-like reaction of tetra-O-acetyl-D-xylopyranase with triphenylphosphine and carbon tetrachloride was used to yield a 2,3,4,tri-O]-methyl-methyl-D−oxidized xyloside.

TL;DR: In this article, the reaction of 1.2:3,4:5,6,7,8,9,10,11,12,14,15,16,17,18,19,20,21,22,23,24,25,26,27,28,29,30,31,32,33,34,35,36,37,38,39,40,41,40

TL;DR: In this article, all possible optically active regioisomers of myo-inositol mono and bisphosphates were synthesized using inositol derivatives suitably protected with various protecting groups (IRns) as key intermediates.