291753-79-2Relevant articles and documents
Regioselective conversion of primary alcohols into iodides in unprotected methyl furanosides and pyranosides
Skaanderup, Philip R.,Poulsen, Carina Storm,Hyldtoft, Lene,Jorgensen, Malene R.,Madsen, Robert
, p. 1721 - 1727 (2002)
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
Vinyl Grignard-Mediated Stereoselective Carbocyclization of Lactone Acetals
Hedberg, Christinne,Estrup, Morten,Eikeland, Espen Z.,Jensen, Henrik H.
, p. 2154 - 2165 (2018/02/23)
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.
Chiron approach to the total synthesis of Amaryllidaceae alkaloid (+)-lycoricidine
Saidhareddy, Puli,Shaw, Arun K.
, p. 6773 - 6779 (2017/10/30)
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
New mannose derivatives: The tetrazole analogue of mannose-6-phosphate as angiogenesis inhibitor
Ionescu, C?t?lina,Sippelli, Simona,Toupet, Lo?c,Barragan-Montero, Véronique
supporting information, p. 636 - 639 (2016/01/09)
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).
Stable analogues of nojirimycin-synthesis and biological evaluation of nojiristegine and manno-nojiristegine
Viuff, Agnete H.,Besenbacher, Louise M.,Kamori, Akiko,Jensen, Mikkel T.,Kilian, Mogens,Kato, Atsushi,Jensen, Henrik H.
, p. 9637 - 9658 (2015/09/28)
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.
NOVEL MANNOPYRANOSIDE DERIVATIVES WITH ANTICANCER ACTIVITY
-
, (2012/11/07)
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
Synthesis of novel sugar-lactam conjugates using the Aube reaction
Kurhade, Suresh E.,Mengawade, Tanaji,Bhuniya, Debnath,Palle, Venkata P.,Reddy, D. Srinivasa
supporting information; experimental part, p. 744 - 747 (2011/04/16)
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.
Efficient synthesis of (6-deoxy-glycopyranosid-6-yl) sulfone derivatives and their effect on Ca2+-ATPase
Mukherjee, Chinmoy,Ghosh, Swatilekha,Nandi, Pinki,Sen, Parimal C.,Misra, Anup Kumar
experimental part, p. 6012 - 6019 (2011/01/13)
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
Synthesis of 1,2-trans C-glycosyl compounds by reductive samariation of glycosyl iodides
Miquel,Doisneau,Beau
, p. 2347 - 2348 (2007/10/03)
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.
