Journal ArticleDOI
Chain elongation of primary alcohols of carbohydrates
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TLDR
In this article, the chain elongation of primary alcohol of saccharides (α- d -ribose, α- d-glucose, β-d -mannose) and disaccharides was achieved via a Mitsunobu reaction using bis(2, 2,2,2-trifluoroethyl) malonate as nucleophile.About:
This article is published in Tetrahedron Letters.The article was published on 2004-09-27. It has received 13 citations till now. The article focuses on the topics: Melibiose & Mitsunobu reaction.read more
Citations
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Journal ArticleDOI
Mitsunobu and Related Reactions: Advances and Applications
TL;DR: This review concludes that Etherification without Cyclization and N-Alkylation should be considered as separate science, and the proposed treatment of Etherification with Cyclization as a separate science should be reconsidered.
Journal ArticleDOI
Synthesis and receptor binding affinity of carboxylate analogues of the mannose 6-phosphate recognition marker.
TL;DR: Four carboxylate analogues of mannose 6-phosphate/insulin-like growth factor II receptor showed a binding affinity for the M6P/IGF2R equivalent to or higher than that of M 6P, which represents a new potential for the lysosomal targeting of enzyme replacement therapy in lysOSomal diseases or to prevent the membrane-associated activities of the M7P/IGF2R.
Journal ArticleDOI
Synthesis and evaluation of non-hydrolyzable d-mannose 6-phosphate surrogates reveal 6-deoxy-6-dicarboxymethyl-d-mannose as a new strong inhibitor of phosphomannose isomerases
Johanna Foret,Benoit de Courcy,Benoit de Courcy,Nohad Gresh,Jean-Philip Piquemal,Laurent Salmon +5 more
TL;DR: 6-deoxy-6-phosphonomethyl-d-mannose appeared as a new strong competitive inhibitor of both S. cerevisiae and E. coli PMIs, and is reported the first malonate-based inhibitor of an aldose-ketose isomerase to date.
Journal ArticleDOI
Microwave-assisted iridium-catalyzed [2+2+2] cycloaddition of resin-bound dipropargylamine with alkynes
TL;DR: The [Ir(COD)Cl] 2 /dppe system effectively catalyzes the solid-phase cycloaddition of resin-bound dipropargylamine with alkynes under microwave conditions as mentioned in this paper.
Journal ArticleDOI
A Mitsunobu route to C-glycosides
Paolo Pasetto,Matthew C. Walczak +1 more
TL;DR: In this article, C-Glycosides were successfully prepared via dehydrative alkylation under Mitsunobu conditions, using substituted sulfonyl methanes as nucleophiles.
References
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Journal ArticleDOI
The Use of Diethyl Azodicarboxylate and Triphenylphosphine in Synthesis and Transformation of Natural Products
TL;DR: In this article, a reagent formed by combining diethyl azodicarboxylate (DEAD) and triphenylphosphine (TPP) could be utilized in the intermolecular dehydration between an alcohol and various acidic components such as carboxylic acids, phosphoric diesters, imides, and active methylene compounds.
Journal ArticleDOI
Preparation of Esters of Carboxylic and Phosphoric Acid via Quaternary Phosphonium Salts
Oyo Mitsunobu,Masaaki Yamada +1 more
TL;DR: In this article, the reaction of carboxylic acid with triphenyl phosphine and diethyl azodicarboxylate in the presence of an alcohol has been studied.
Journal ArticleDOI
Progress in the mitsunobu reaction. a review
TL;DR: A review of progress in the MITSUNOBU this article reaction can be found in this article, with a focus on the MIT SUNOBU reaction and a review of the progress.
Journal ArticleDOI
A mannose-6-phosphonate–cholesterylamineconjugate as a specific molecular adhesive linking cancer cells withvesicles
Veronique Barragan,Fredric M. Menger,Kevin L. Caran,Carole Vidil,Alain Morère,Jean-Louis Montero +5 more
TL;DR: A hydrolytically stable sugar phosphonate coupled to a steroid via a long and semi-rigid spacer binds both to the mannose-6-phosphonate receptors of certain cancer cells and to the lipid bilayer of vesicles, thereby serving as a multivalent adhesive between cell and vesicle surfaces.
Journal ArticleDOI
Synthesis and Biological Activity of Phosphonate Analogs of Mannose 6-Phosphate (M6P)
Carole Vidil,Alain Morère,Marcel Garcia,Véronique Barragan,Bassou Hamdaoui,Henri Rochefort,Jean-Louis Montero +6 more
TL;DR: Two phosphonate analogs of mannose 6-phosphate (M6P) have been synthesized by Wittig-Horner reaction at position 6 of a sugar aldehyde.
Related Papers (5)
Chain elongation by use of an iron carbonyl reagent: A facile synthesis of 6-deoxyheptosiduronic acids
Hans H. Baer,Hanna R. Hanna +1 more