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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9 citations
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TL;DR: The 1,3-diaza-2-azoniaallene salt 3a reacts stereoselectively with glycals (5a,b) to afford pyrano[2, 3-d]-1, 2, 3 -triazolium salts as mentioned in this paper.
Abstract: The 1,3-diaza-2-azoniaallene salt 3a reacts stereoselectively with glycals (5a—e) to afford pyrano[2,3-d]-1,2,3- triazolium salts 6a—e. In contrast to other 1,3-dipolar cycloadditions of glycals reported so far, the stereoselectivity of compounds 6 is not determined by the substituent on C-3 of the glycal. Both cis (6a,b) and trans (6d,e) substitutions on C-7 and C-7a were found for bicyclic compounds 6 (crystal structure of 6a). Under the influence of acid 6e opens the pyran ring to give the triazolium salt 9. Addition of antimony pentachloride to a solution of the glycal 5e and the chlorotriazene 2a results in the formation of the pyranotriazene 12 containing two triazene units. In the presence of acid the pyranotriazene 6c reacts with alcohols to afford 2-hydrazino glycosides 13a,b, 15, which with zinc dust in acetic acid are reduced to 2-amino glycosides 14a,b.
9 citations
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9 citations
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TL;DR: A three‐step sequence affects the regio‐ and stereospecific elaboration of an aryl C‐aminoglycoside from a simple aminoglycal and a quinone to give a product with a trans‐trans stereochemical relationship between the substituents, appropriate for compounds in the ravidomycin series.
9 citations
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TL;DR: 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-glycosides
9 citations