Journal ArticleDOI
Mitsunobu reaction of 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-hydroxymethyl-hex-1-enitols and 1,5-anhydro-2-deoxy-4,6-O-protected-hex-1-enitols. A novel method for the synthesis of 2-C-methylene glycosides and an useful alternative to Ferrier rearrangement
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TLDR
In this paper, a simple and convenient method for the synthesis of aryl-3,4,6-tri-O-benzyl-2-deoxy-methylene-hexopyranosides 5,6 and 7, glycosides which are not accessible by the conventional Ferrier rearrangement, has been described based on the Mitsunobu reaction of alcohols 3 and 4 with substituted phenols.About:
This article is published in Tetrahedron.The article was published on 1995-01-02. It has received 32 citations till now. The article focuses on the topics: Ferrier rearrangement & Mitsunobu reaction.read more
Citations
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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
Recent Developments in the Ferrier Rearrangement
TL;DR: A review of recent developments in the use of promoters for the Ferrier rearrangement of O-, N-, C- and S-nucleophiles with glycals can be found in this paper.
Journal ArticleDOI
Sterically biased 3,3-sigmatropic rearrangement of chiral allylic azides: application to the total syntheses of alkaloids.
Sophie Lauzon,Francois Tremblay,David Gagnon,Cédrickx Godbout,Christine Chabot,Catherine Mercier-Shanks,Stéphane Perreault,Helene DeSeve,Claude Spino +8 more
TL;DR: A tandem Mitsunobu/3,3-sigmatropic rearrangement of allylic azides on a chiral auxiliary system that favors one regioisomer thanks to its exceptional steric bias is described.
Journal ArticleDOI
New optically pure sugar hydroperoxides. Synhtesis and use for enantioselective oxygen transfer
Hans-Jürgen Hamann,Eugen Höft,Danuta Mostowicz,Anatoly Mishnev,Zofia Urbańczyk-Lipkowska,Marek Chmielewski +5 more
TL;DR: In this paper, 2-Deoxy-2-C-methylene methyl glycosides undergo oxidation with hydrogen peroxide in the presence of molybdenum trioxide as catalyst to afford the corresponding anomeric hydroperoxides.
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Sterically biased 3,3-sigmatropic rearrangement of azides: efficient preparation of nonracemic alpha-amino acids and heterocycles.
TL;DR: Homochiral alpha-amino acids, heterocycles, and carbocycles are efficiently constructed via a short sequence of reactions starting from the chiral auxiliary p-menthane-3-carboxaldehyde that procures enantiomerically enriched allylic azides.
References
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Journal ArticleDOI
Nucleosides and nucleotides. 97. Synthesis of new broad spectrum antineoplastic nucleosides, 2'-deoxy-2'-methylidenecytidine (DMDC) and its derivatives.
TL;DR: DMDC as well as 2'-deoxy-2'-methylidene-5-fluorocytidine (19a) showed potent antileukemic activity against murine L 1210 cells in culture and in vivo antitumor activity of DMDC against L1210 was also described.
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Palladium(0)-based approach to functionalized C-glycopyranosides
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A highly stereoselective synthesis of aryl 2-deoxy-.beta.-glycosides via the Mitsunobu reaction
William R. Roush,Xiao Fa Lin +1 more
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A Rapid Route to Hex-1-enopyran-3-uloses
TL;DR: In this article, it was shown that triacetyl glucal can be converted to 6-O-triphenylmethyl ether or 6 O-benzoyl ester to promote solubility in chloroform, and the derivatives are oxidized in that solvent in 12 h or less.
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Vilsmeier-haack reactoin of glycals-a short route to C-2-formyl glycals☆
TL;DR: A short and straightforward route has been accomplished for the synthesis of C-2-formyl glycals by a Vilsmeier-Haack reaction of glycals.
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Stereoselective palladium-catalyzed O-glycosylation using glycals
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