- Boronic esters as protective groups in carbohydrate chemistry: processes for acylation, silylation and alkylation of glycoside-derived boronates
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Procedures for selective installation of acyl, silyl ether and para-methoxybenzyl (PMB) ether groups to glycoside substrates have been developed, employing phenylboronic esters as protected intermediates. The sequence of boronic ester formation, functiona
- Mancini, Ross S.,Lee, Jessica B.,Taylor, Mark S.
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p. 132 - 143
(2016/12/27)
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- New antitumour agents with α,β-unsaturated δ-lactone scaffold: Synthesis and antiproliferative activity of (?)-cleistenolide and analogues
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A stereoselective total synthesis of (?)-cleistenolide (1) from D-glucose has been achieved. This new approach for the synthesis of (?)-cleistenolide and analogues involves a one-C-atom degradation of the chiral precursor, (Z)-selective Wittig olefination, followed by the final δ-lactonisation. Synthesized compounds showed potent growth inhibitory effects against selected human tumour cell lines, especially 2,4,6-trichlorobenzoyl derivative 12, which in the culture of MDA-MB 231 cells displayed the highest activity (IC500.02?μM) of all compounds under evaluation. A preliminary SAR study reveals the structural features that are beneficial for antiproliferative activity of synthesized δ-lactones, such as presence of either electron-withdrawing or electron-donating substituents in the aromatic ring, as well as the presence of cinnamoyl functionality instead of benzoyl group at the O-7 position.
- Benedekovi?, Goran,Kova?evi?, Ivana,Popsavin, Mirjana,Francuz, Jovana,Koji?, Vesna,Bogdanovi?, Gordana,Popsavin, Velimir
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supporting information
p. 3318 - 3321
(2016/07/12)
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- A concise total synthesis of cleistenolide
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A concise total synthesis of cleistenolide has been achieved from D-glucose. The synthesis of cleistenolide proceeds in six steps from D-glucose diacetonide in 42.5% overall yield. Selective benzoylation and Still-Gennari olefination are the key reactions involved in the synthesis.
- Reddy, A. Bal,Kumara Swamy,Yadav, Jhillu Singh
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p. 788 - 790
(2016/07/29)
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- Modifying the regioselectivity of glycosynthase reactions through changes in the acceptor
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Successful glycosynthase-mediated reactions have been performed on 6-O-benzyl-, 6-O-(4-nitrobenzyl)-, and 6-O-benzoyl-D-glucopyranose to give 1,2-β- and 1,3-β-D-glycosylated products; 4-O-benzyl-D-xylopyranose gave only a 1,2-β-glycosylated product. A rat
- Stick, Robert V.,Stubbs, Keith A.,Watts, Andrew G.
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p. 779 - 786
(2007/10/03)
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- Control of regioselectivity in reactions of dialkylstannylene acetals. Part I. A dramatic reversal of regioselectivity in mono-p-toluenesulfonation reactions
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The regioselectivities of p-toluenesulfonation reactions of dialkylstannylene acetals obtained from a number of carbohydrate-derived terminal 1,2-diols in the absence of added nucleophiles have been explored as functions of the carbohydrate structure, the
- Kong, Xianqi,Grindley, T. Bruce
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p. 2396 - 2404
(2007/10/02)
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- Regioselective monotosylation of non-protected and partially protected glycosides by the dibutyltin oxide method
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Tosylation of non-protected glycopyranosides with p-toluenesulfonyl chloride in the presence of 4-dimethylaminopyridine, after activiation of the glycosides by dibutyltin oxide, gave mono-O-tosylates in good yield. The regioselectivity in this tosylation
- Tsuda,Nishimura,Kobayashi,Sato,Kanemitsu
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p. 2883 - 2887
(2007/10/02)
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- DIPHENYLMETHYLATION OF CARBOHYDRATE HYDROXYL GROUPS BY THE REACTION WITH DIAZO(DIPHENYL)METHANE
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Diphenylmetylation of carbohydrate hydroxyl groups may be effected by the thermal reaction with diazo(diphenyl)methane in absence of catalysts.Migration of the labile ester groups of methyl 2,3,4-tri-O-acetyl-α-D-glucopyranoside and 3-O-benzoyl-1,2-O-isopropylidene-α-D-glucofuranose does not occur during diphenylmethylation by this procedure.The diphenylmethyl group may be readily removed by catalytic hydrogenolysis, and is sufficiently acid-stable to enable the selective hydrolysis of acetal groups.Its use as an O-4 protecting-group and as a non-participating O-2 protecting-group in α-glucoside synthesis has been demonstrated in syntheses of methyl 2,3,6-tri-O-methyl-α-D-glucopyranoside and kojibiose octa-acetate, respectively.
- Jackson, Graham,Jones, Haydn F.,Petursson, Sigthor,Webber, John M.
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p. 147 - 158
(2007/10/02)
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- A Simple Regioselective Partial Hydrolysis of Di-O-isopropylidene Monosaccharides with Copper(II) Ion
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Copper(II) ion was found to be effective for regioselective removal of the 5,6-O-isopropylidene group of α-D-mannose and α-D-glucose derivatives in alcohols at ambient temperature.
- Iwata, Masaaki,Ohrui, Hiroshi
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p. 2837 - 2838
(2007/10/02)
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