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: A multi-gram epoxidation of 3,4,6-tri-O-benzyl-D-glucal and D-galactal with dimethyldioxirane with DMDO generated in situ from Oxone/acetone in a biphasic system resulted in the formation of the corresponding 1,2-anhydrosugars in a 99% yield and 100% selectivity.
56 citations
TL;DR: This contribution describes the results of a new research effort in the laboratory aimed at the synthesis of novel aminoglycosides and amino-C-glycosides, which relies on a surprising and unprecedented formation of glycal triazolines via an inverse electron demand dipolar cycloaddition of glucal.
Abstract: This contribution describes the results of a new research effort in our laboratory aimed at the synthesis of novel aminoglycosides and amino-C-glycosides. Despite the importance of such compounds, and the previous development of some methodological solutions, this remains an important area of research. Notable features of our approach, which is distinct from and complementary to previous efforts, are the following: (1) Reliance on a surprising and unprecedented formation of glycal triazolines via an inverse electron demand dipolar cycloaddition of glucal. We believe this desirable transformation has not previously been discovered because of the unusual selection of substrates and solvent required. (2) Very mild reaction conditions. An initial thermal cycloaddition is carried out in an inert solvent, the triazoline generated is photochemically converted to a reactive aziridine, and the crude aziridine undergoes ring opening at room temperature in the presence of a nucleophile and a mild Lewis acid catalys...
56 citations
TL;DR: In this paper, a method for C-glycosidation with various silylacetylenes to d -glucal by iodine molecule via iodo-oxonium intermediates provided exclusively the α-acetylene glycoside products.
55 citations
TL;DR: In this article, the authors investigated the regioselectivity of the glycosylation reaction using p -nitrophenyl β-d -galactopyranoside, β- d -mannopyranoyl fluoride and d -glucal donors and acceptors.
53 citations
52 citations