Topic
Glycal
About: Glycal is a research topic. Over the lifetime, 897 publications have been published within this topic receiving 17422 citations.
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TL;DR: A phase-trafficking methodology that relies upon nucleophilic interception of the 1,2 anhydrosugar resulting from oxidation of the glycal has been developed and offers advantages over solid-phase methods that require more than 5 equiv of donor.
Abstract: High mannose glycans composed of α (1→2) and α (1→6) branched sugars are important components of the HIV-associated envelope glycoprotein, gp120. These substructures can be efficiently prepared in solution from glycosyl iodide precursors requiring only a slight excess of the iodide donor, which offers advantages over solid-phase methods that require more than 5 equiv of donor. During the reaction, excess iodide is converted to a glycal that is not easily separated from the desired disaccharide. To overcome this difficulty, a phase-trafficking methodology that relies upon nucleophilic interception of the 1,2 anhydrosugar resulting from oxidation of the glycal has been developed.
22 citations
TL;DR: Diastereoisomeric D,L-N-Cbz-imino glycal-derived allyl epoxides 5 and 6 have been synthesized, and their addition reactions with alcohols examined, leading to a new, completely regioselective 1,4-addition process which proceeds with complete substrate-dependent stereoselectivity.
22 citations
TL;DR: Trans-addition of iodoazide to the double bond of 3,4,6-tri-O -acetyl-1,5-anhydro-d - arabino -hex-1-enitol yielded 2-deoxy-2-iodoglycosyl azides, which are precursors of 1,2- trans -2-amino-2deoxyglycopyranosides when treated by an alcohol in the presence of triphenylphosphine as mentioned in this paper.
22 citations
TL;DR: The 4-thio-beta-D-ribofuranosyl derivatives of uracil, thymine, N (4) -acetylcytosine, 6-chloropurine, and 2-amino-6-chlorOPurine were synthesized and can be extended to the beta-selective synthesis of 4'-thIO-C-ribonucleosides.
Abstract: Upon reacting 3,5-O-(di-tert-butyl)silylene-4-thiofuranoid glycal S-oxide (6) with Ac2O/TMSOAc/BF3·OEt2 in CH2Cl2, the additive Pummerer reaction proceeded to furnish the corresponding 1,2-di-O-acetyl-4-thioribofuranose 7 Compound 7 serves as a highly β-selective glycosyl donor in the Vorbruggen condensation carried out in the presence of TMSOTf Thus, the 4-thio-β-d-ribofuranosyl derivatives of uracil, thymine, N(4)-acetylcytosine, 6-chloropurine, and 2-amino-6-chloropurine were synthesized The use of 7 can be extended to the β-selective synthesis of 4′-thio-C-ribonucleosides
22 citations
22 citations