Journal ArticleDOI
Stereoselective synthesis of C-2-methylene and C-2-methyl-C-glycosides by Claisen rearrangement of 2-vinyloxymethyl glycals
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An efficient protocol for the stereoselective synthesis of C-2-methylene-α and -β-C-glycosides by a Claisen rearrangement of 2-vinyloxymethyl glycal derivatives is reported in this article.Abstract:
An efficient protocol for the stereoselective synthesis of C-2-methylene-α- and -β-C-glycosides by a Claisen rearrangement of 2-vinyloxymethyl glycal derivatives is reported A plausible mechanism for the formation of α-selective-C-glycoside was proposed The methodology was further extended to the high diastereoselective synthesis of C-2-methyl-C-glycosidesread more
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Recent Advances in the Chemical Synthesis of C-Glycosides
TL;DR: Mechanistically, C-glycosylation reactions can involve glycosyl electrophilic/cationic species, anionic species, radical species, or transition-metal complexes, which are discussed as subcategories under each type of sugar precursor.
Journal ArticleDOI
Recent Developments in the Synthesis of 2‐C‐Branched and 1,2‐Annulated Carbohydrates
TL;DR: The importance of carbohydrate chemistry in biological and medicinal chemistry has led to enormous developments in the synthesis of carbohydrate mimics as mentioned in this paper, and the recent synthetic efforts in this area and puts the subject matter into proper perspective for future developments.
Journal ArticleDOI
Synthesis of Dihydroxymethyl Dihydroxypyrrolidines and Steviamine Analogues from C-2 Formyl Glycals
TL;DR: The newly synthesized molecules have been evaluated for glycosidase inhibition against 6 commercially available enzymes and found to be active in the micromolar range, where one of the steviamine analogues showed good and selective inhibition of β-mannosidase (Helix pomatia).
Journal ArticleDOI
Applications of 2-C-Formyl-Glycals in Organic Synthesis
TL;DR: Recent developments in the synthesis and applications of 2-C-formyl-glycals, the versatile chiral intermediates, are summarized in this review.
Journal ArticleDOI
Stereoselective Construction of 2,8-Dioxabicyclo[3.3.1]nonane/nonene Systems from 3-C-Branched Glycals†
TL;DR: In this article, a stereoselective approach for the formation of 2,8-dioxabicyclo[3.3.1]nonane/nonene frameworks through formation of 3-C-branched glycals encompassing the Claisen rearrangement of the carbohydrate-derived allyl-vinyl ethers and TMSOTf-catalyzed acetalization reactions as key steps is revealed.
References
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Reference BookDOI
Preparative carbohydrate chemistry
TL;DR: The authors discusses the reactions and derivative forms of carbohydrates and discusses commonly used methods and procedures, and illustrates bond-forming reactions of SN2 types, free radicals, chain extensions, and branching.
Journal ArticleDOI
Über Umlagerung von Phenol‐allyläthern in C‐Allyl‐phenole
TL;DR: Salmiak as mentioned in this paper verwandelter Verbindungen in 0-Alkylderivaten and C-Derivate umzulagern, tritt diese Neigung bei den 0 A 11 y lderivaten i n stitrkstem Mn5e hervor.
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Stereochemistry of Nucleophilic Substitution Reactions Depending upon Substituent: Evidence for Electrostatic Stabilization of Pseudoaxial Conformers of Oxocarbenium Ions by Heteroatom Substituents
TL;DR: Lewis acid-mediated nucleophilic substitution reactions of substituted tetrahydropyran acetates reveal that the conformational preferences of six-membered-ring cations depend significantly upon the electronic nature of the substituent, and reinforces the idea that ground-state conformational effects need to be considered along with steric approach considerations.