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 systematic stereocontrolled synthesis of benzannulated spiroketals has been developed, using kinetic spirocyclization reactions of glycal epoxides, leading to a new AcOH-induced cyclization and valuable insights into the reactivity and conformations of these systems.
43 citations
TL;DR: Two novel routes to C-linked glycosyl amino acids are described; the first involves elaboration of an exo-glycal and subsequent Ramberg–Backlund rearrangement of a sulfone intermediate to give, after functional group manipulation, a protected C-glycosyl serine.
43 citations
TL;DR: Glycal derivatives of N-acetylneuraminic acid were prepared and their N-iodosuccinimide-mediated glycosylation shown to proceed only with most reactive alcohols, which led to both the anomeric phenylthioglycosides or N dcety Ineuraminic Acid.
43 citations
TL;DR: In this article, a variety of 1-thiohex-2-enopyranosides have been prepared from their corresponding 3-O-methyl- or 3O-acetyl glycals by using trimethylsilyl thiols catalyzed by BF/sub 3/ etherate.
Abstract: A variety of 1-thiohex-2-enopyranosides have been prepared from their corresponding 3-O-methyl- or 3-O-acetylglycals by using trimethylsilyl thiols catalyzed by BF/sub 3/ etherate. This method is regioselective for thiolation at C-1 in contrast to the same reaction with thiols which produces C-3 products under thermodynamic control. The stereoselectivity of the reaction depended on the choice of trimethylsily thiol and the leaving group at C-3 of the glycal. ((Trimethylsilyl)thio)benzene gave ..cap alpha..-anomers as the only products, whereas (thionacetoxy)trimethylsilane gave more ..beta..-anomer products from 3-O-methylglycals than from 3-O-acetylglycals. Examples reported include the synthesis of S-(2'-pyridyl) 2,3,6-trideoxy-4,6-di-O-acetyl-1-thio-..cap alpha..-D-erythro-hex-2-enopyranoside (1), S-phenyl 2,3,6-trideoxy-4-O-methyl-1-thio-..cap alpha..-L-erythro-hex-2-enopyranoside (15), S-acetyl 2,3,6-trideoxy-4-O-methyl-1-thio-..beta..-L-erythro-hex-2-enopyranoside (16), S-acetyl 2,3-dideoxy-4,6-di-O-methyl-1-thio-..cap alpha..,..beta..-D-erythro-hex-2-enopyranosides (17, 18), S-acetyl 2,3-dideoxy-4,6-di-O-acetyl-1-thio-..cap alpha..,-..beta..-D-erythro-hex-enopyranosides (19, 20), and S-acetyl 2,3,6-trideoxy-4-O-acetyl-1-thiol-..cap alpha..,..beta..-L-erythro-hex-2-enopyranosides (21,22). 24 references, 3 figures, 2 tables.
43 citations