- Regioselective conversion of primary alcohols into iodides in unprotected methyl furanosides and pyranosides
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Two methods are described for the regioselective displacement of the primary hydroxy group in methyl glycosides with iodide. The first method is a modification of a literature procedure employing triphenylphosphine and iodine, where purification has been
- Skaanderup, Philip R.,Poulsen, Carina Storm,Hyldtoft, Lene,Jorgensen, Malene R.,Madsen, Robert
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- Vinyl Grignard-Mediated Stereoselective Carbocyclization of Lactone Acetals
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A novel Ferrier-type carbocyclization is reported. It involves a carbohydrate-derived lactone acetal synthesized from methyl α-d-glucopyranoside, which upon treatment with excess vinylmagnesium bromide provides a highly substituted carbocyclic product as a single stereoisomer. The yield is greatly increased when N,N,N′,N′-tetramethylethylenediamine is added to the reaction mixture. Optimized reaction conditions have been applied to lactone acetals derived from other carbohydrates. Based on the obtained results, a possible reaction mechanism has been proposed. Furthermore, scalability of the reaction up to 15 g scale and derivatization of the carbocyclic product has been demonstrated, including the formation of a rare trans-bicyclo[4.3.0]nonene scaffold via a ring-closing metathesis. The structure of this and all carbocyclic products were confirmed by X-ray crystallographic analysis.
- Hedberg, Christinne,Estrup, Morten,Eikeland, Espen Z.,Jensen, Henrik H.
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p. 2154 - 2165
(2018/02/23)
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- Chiron approach to the total synthesis of Amaryllidaceae alkaloid (+)-lycoricidine
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A highly stereoselective total synthesis of Amaryllidaceae alkaloid starting from α-D-galactopyranoside has been described. The salient features of this total synthesis are Ferrier carbocyclization reaction for the synthesis of ring A and Suzuki Miyaura c
- Saidhareddy, Puli,Shaw, Arun K.
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p. 6773 - 6779
(2017/10/30)
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- New mannose derivatives: The tetrazole analogue of mannose-6-phosphate as angiogenesis inhibitor
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Two novel compounds with mannose-derived structure, bearing a tetrazole (compound 3) and a sulfone group (compound 4) in terminal position, have been prepared from methyl α-d-mannopyranoside in reduced number of steps. The angiogenic activity of 3 and 4 has been screened using the chick chorioallantoic membrane (CAM) method. Tetrazole 3 has been identified to possess a promising bioactivity, being identified as angiogenesis inhibitor, with 68% of neovascular vessels when compared to control (PBS).
- Ionescu, C?t?lina,Sippelli, Simona,Toupet, Lo?c,Barragan-Montero, Véronique
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p. 636 - 639
(2016/01/09)
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- Stable analogues of nojirimycin-synthesis and biological evaluation of nojiristegine and manno-nojiristegine
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Two novel iminosugars called nojiristegines, being structural hybrids between nor-tropane alkaloid calystegine and nojirimycins, have been synthesised and found to be stable molecules despite the presence of a hemiaminal functionality. The synthesised iminosugars were evaluated against a panel of glycosidases and the best inhibition (IC50), found against α-glucosidases, was in the micromolar region. The compounds were also evaluated as potential antibiotics but no useful level of activity was observed.
- Viuff, Agnete H.,Besenbacher, Louise M.,Kamori, Akiko,Jensen, Mikkel T.,Kilian, Mogens,Kato, Atsushi,Jensen, Henrik H.
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p. 9637 - 9658
(2015/09/28)
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- NOVEL MANNOPYRANOSIDE DERIVATIVES WITH ANTICANCER ACTIVITY
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The present invention relates to mannopyranoside-derived compounds and to the use thereof as medicaments, in particular in the treatment of cancer diseases, and also to the method for preparing same and to pharmaceutical compositions comprising such compo
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- Synthesis of novel sugar-lactam conjugates using the Aube reaction
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An efficient and convenient method for the synthesis of sugar-lactam conjugates is reported starting from readily available sugar azides using the Aube reaction. Cyclic azido alcohols are used in the Aube reaction for the first time in a carbohydrate setting. The resulting glycoconjugates could be further used to increase the chemical diversity on the sugar backbone, and may find potential applications as glycomimetics, peptidomimetics, in glycotargeting and in CNS drug delivery.
- Kurhade, Suresh E.,Mengawade, Tanaji,Bhuniya, Debnath,Palle, Venkata P.,Reddy, D. Srinivasa
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p. 744 - 747
(2011/04/16)
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- Efficient synthesis of (6-deoxy-glycopyranosid-6-yl) sulfone derivatives and their effect on Ca2+-ATPase
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Synthesis of a series of novel (6-deoxy-glycopyranosid-6-yl) sulfone derivatives has been achieved using a general synthetic strategy. Yields were excellent in every case. The synthetic compounds were evaluated for their biological potential against Casu
- Mukherjee, Chinmoy,Ghosh, Swatilekha,Nandi, Pinki,Sen, Parimal C.,Misra, Anup Kumar
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experimental part
p. 6012 - 6019
(2011/01/13)
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- Vitamin b12 catalysis of zinc-mediated 6-deoxy-6-iodopyranoside fragmentation: A mild and convenient preparation of ω-unsaturated hexose derivatives (5-hexenoses)
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The known zinc-mediated preparation of 5-hexenoses by fragmentation of 6-iodopyranosides can be performed in a simple, fast, and mild way, with less side reactions, when vitamin B12 is employed as a catalyst.
- Kleban, Martin,Kautz, Ulrich,Greul, J?rg,Hilgers, Petra,Kugler, Rolf,Dong, Han-Qing,J?ger, Volker
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p. 1027 - 1033
(2007/10/03)
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- The cobalt-catalyzed oxygenative radical route from hexopyranosides to carbapentofuranoses
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Cobalt-catalyzed radical cyclization/oxygenation of various 6-iodohex-1-enitols gave in one step the carbocyclic analogs of pentofuranoses. The reaction was run under very mild conditions and gave moderate to good yields of carbapentofuranoses within a few hours. All the possible 6-iodohex-1-enitol stereoisomers were prepared, and the influence of relative configurations and protecting groups was studied.
- Desire, Jerome,Prandi, Jacques
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p. 3075 - 3084
(2007/10/03)
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- Synthesis of 1,2-trans C-glycosyl compounds by reductive samariation of glycosyl iodides
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Reductive samariation of per-O-trimethylsilyl or benzyl glycopyranosyl iodides in the presence of carbonyl compounds provides the corresponding 1,2-trans-C-glycosyl compounds in good yields.
- Miquel,Doisneau,Beau
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p. 2347 - 2348
(2007/10/03)
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- Novel carbocyclic ring closure of hex-5-enopyranosides
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Retention of configuration at the anomeric carbon atom is observed for a novel rearrangement of carbohydrates. The readily accessible vinyl acetal 1 undergoes a triisobutylaluminum-assisted, stereoselective transposition of an oxygen atom on the ring with
- Das,Mallet,Sinay
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p. 493 - 496
(2007/10/03)
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