Journal ArticleDOI
A new ferrier system: 2-C-acetoxymethylglycals. A covenient entry to 2-C-methylene glycosides
C. Booma,K. K. Balasubramanian +1 more
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In this paper, the synthesis of tri-O-benzyl-2-C-acetoxymethyl glycals and subsequent Ferrier rearangement to give 2C-methylene glycosides is described.Abstract:
Syntheis of tri-O-benzyl-2-C-acetoxymethylglycals and subsequent Ferrier rearangement to give 2-C-methylene glycosides is described.read more
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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.
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Application of an enyne metathesis/Diels-Alder cycloaddition sequence: a new versatile approach to the syntheses of C-aryl glycosides and spiro-C-aryl glycosides.
TL;DR: An efficient approach for the synthesis of a variety of C-aryl and spiro-C-aryl glycosides is described, which relies on a sequential enyne metathesis to generate the 1,3-diene moiety and Diels-Alder reaction with different dienophiles followed by aromatisation.
Journal ArticleDOI
Synthesis of oxepines and 2-branched pyranosides from a d-glucal-derived gem-dibromo-1,2-cyclopropanated sugar.
TL;DR: The conversion of cyclopropane-fused carbohydrates into oxepines is an attractive method for accessing diverse members of the septanoside family of carbohydrate mimetics, and 2-Bromooxepines are obtained through silver(I)-promoted thermal ring expansion of a d-glucal-derived gem-dihalocyclopropanated sugar.
Journal ArticleDOI
2‐C‐Formyl Glycals: Emerging Chiral Synthons in Organic Synthesis
TL;DR: In this article, a new class of 2-C-formyl glycals, incorporating an α,β-unsaturated carbonyl system, have been proposed as potential synthons for numerous organic transformations.
Journal ArticleDOI
Synthesis of C-2 Methylene O- and C-Glycosides and Sugar Derived α-Methylene-δ-valerolactones from C-2-Acetoxymethyl Glycals☆
TL;DR: In this paper, C-2-Methylene O- and C-glycosides are readily synthesized from C-acetoxymethyl glycals using Nafion-H®, montmorillonite K-10, LiClO4 (0.07m) in dichloromethane and Pd(PPh3)4 as catalysts.
References
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Journal ArticleDOI
Titanium-mediated methylene transfer reactions on sugar esters, lactones, and uloses
Journal ArticleDOI
(.+-.)-4-tert-Butyl-3-cyano-1-(4-ethynylphenyl)-2,6,7-trioxabicyclo[2.2.2]octane: synthesis of a remarkably potent GABAA receptor antagonist
Journal ArticleDOI
REACTIONS OF 2-ACETOXY-4,6-DI-O-ACETYL-3-O-(2,6-DICHLOROBENZOYL)-D-GLUCAL, TRI-O-ACETYL-3-DEOXY-α-D-erythro-HEX-2-ENOPYRANOSYL CHLORIDE, AND RELATED COMPOUNDS
R. U. Lemieux,R. J. Bose +1 more
TL;DR: In this article, the replacement of the tosyloxy group by the diethylamine was introduced, which led to products resulting from the substitution of the TOS group with the LD group.
Journal ArticleDOI
Branched-chain 2-deoxy sugars. V. Application of the Wittig reaction to methyl 3,4-O-isopropylidene-β-D-erythro-pentopyranosid-2-ulose and attempted synthesis of nucleosides of 2-deoxy-2-C-methylpentoses
Alex Rosenthal,Matej Sprinzl +1 more
TL;DR: In this article, a mixture of 2-deoxy-2-C-methyl pentoses was synthesized in the presence of H-butyllithium tetroxide in 55% yield with the preponderant product having the D-ribo configuration.
Journal ArticleDOI
A regiospecific synthesis of unsaturated nucleosides, carbohydrates and other olefins
TL;DR: Vicinal disubstituted nucleosides, carbohydrates and cyclohexane derivatives with a pair of radical leaving groups have been successfully converted to the corresponding olefins in high yields (60-90%) without observed side products, by reaction with tri-n-butyltin hydride and azobisisobutyronitrile in an appropriate solvent as discussed by the authors.