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: Treatment of acetylated phenyl thioglycoside of N-acetylneuraminic acid with MCPBA in CH2Cl2 affords quantitatively mixtures of the respective sulfone and glycal free from the sulfoxide that can be regarded as a new method for the preparation of sialic acid glycals.
Abstract: Treatment of acetylated phenyl thioglycoside of N-acetylneuraminic acid with m-chloroperbenzoic acid (MCPBA) in CH2Cl2 affords quantitatively mixtures of the respective sulfone and glycal free from the sulfoxide. The outcome of the reaction does not depend on the anomeric configuration of the starting thioglycoside. The sulfone can be selectively prepared (yield ∼100%) by oxidation with an excess of MCPBA and NaHCO3. In the presence of pyridine (2 equiv.) and MCPBA (2 equiv.), the major product is glycal (yields 81—88%). This version of the reaction can be regarded as a new method for the preparation of sialic acid glycals.
5 citations
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TL;DR: In this paper, it was shown that resume chloroacetates are susceptible to regioselective deprotectton by hydraztne acetate, and provide an interesting tool for the synthesis of monomers suitably tailored for the preparation of complex oligosaccharides.
5 citations
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TL;DR: In this paper, a class of organocatalysts that are highly active for the conversion of 2'-deoxynucleosides to furanoid glycals have been discovered.
Abstract: A class of organocatalysts that are highly active for the conversion of 2'-deoxynucleosides to furanoid glycals have been discovered. These phosphorimides, (Ph2PS)2NH and (Ph2PSe)2NH, were shown to effectively mediate persilylation of 2'-deoxynucleosides allowing the elimination of the nucleobase giving the corresponding glycal. These mild conditions were demonstrated in the syntheses of glycals with various substitution patterns while minimizing the formation of undesired byproducts and expanding the scope of this methodology.
5 citations
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TL;DR: The synthesis is based on Heck-coupling between N-protected pseudoisocytosine and a silyl protected furanoid glycal and the corresponding phosphoramidite building block is obtained in 5 steps and an overall yield of 28%.
Abstract: A novel synthesis of 2'-deoxypseudoisocytidine as well as of its phosphoramidite building block for oligonucleotide synthesis is presented. The synthesis is based on Heck-coupling between N-protected pseudoisocytosine and a silyl protected furanoid glycal. With this procedure the corresponding phosphoramidite building block is obtained in 5 steps and an overall yield of 28%.
5 citations
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TL;DR: Novel bridging nucleoside analogues were prepared by cycloaddition reactions between pyranose glycals and barbiturate-derived, reactive thionoimides in modest yields and several of the compounds showed moderate activities against HIV-1 in primary human lymphocytes.
5 citations