Topic
Glucal
About: Glucal is a research topic. Over the lifetime, 590 publications have been published within this topic receiving 8960 citations. The topic is also known as: D-glucal.
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TL;DR: In this article, the authors show that the initial step to consistently be the capture of a bromonium ion by C-2 from the axial side, followed by a trans-addition of ROH, and that fluoro-acetoxylations of the same glucal esters invariably lead to cisaddition products due to a quasi-concerted SET induced mechanism involving a solvent cage-trapped biradical.
Abstract: While the alkoxybromination of glucal and 2-acyloxyglucal esters leads to 2-bromo-2-deoxy-α- d -glycosides and α- d -glycosulosyl bromides, respectively, the exposure of 2-acetamido- d -glucal triacetate to NBS/ROH yields 2-O-alkyl-2-C-acetamido-α- d -mannosyl bromides. Although the final products of these reactions are distinctly different, mechanistic considerations show the initial step to consistently be the capture of a bromonium ion by C-2 from the axial side, followed by a trans-addition of ROH. In contrast, fluoro-acetoxylations of the same glucal esters invariably lead to cis-addition products due to a quasi-concerted SET-induced mechanism involving a solvent cage-trapped biradical.
4 citations
TL;DR: Cyclopropanation of 4,6-O-benzylidene-D-glucal, followed by tributylstannyl radical-mediated regioselective ring opening of the 1,2-cyclopropano sugar led to a 2, 6-anhydro-1-deoxyheptose, (a "methyl C-beta- D-glycoside").
3 citations
3 citations
TL;DR: A large difference in the N-terminal peptide sequence of both lipases resulted in a strong difference in catalytic properties between immobilized enzymes, with ROLpp being the most active, specific and regioselective heterogeneous biocatalyst in the hydrolysis of lactal hexaacetate.
3 citations
TL;DR: X-ray crystallography and 1H NMR spectroscopy indicate that the conformations of both rings A and B and the relative orientation of the rings in the C-linked disaccharide 1,3,4,6-tetra-O-acetyl-2-C-(4, 6-di-Oacetyl)-2,3-dideoxy-α-D-erythro-hex-hex 2-enopyranosyl) in solution are virtually identical to the crystalline structure as mentioned in this paper.
3 citations