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: In this article, the uncatalysed displacement of allylic benzoyloxy groups with azide in unsaturated sugars has been studied by using hexamethylphosphoramide as solvent.
Abstract: The uncatalysed displacement of allylic benzoyloxy groups with azide in unsaturated sugars has been studied by using hexamethylphosphoramide as solvent. Tri-O-benzoylglycals and 4,6-O-benzylidene-3-O-benzoylglycals were investigated. The former gave rise to mixtures of 3-azido-glycals and hex-2-enopyranosyl azides, whereas the latter gave only glycal products. The mechanism of the reactions is considered in some detail. Displacements on allylic trimethylsilyl ethers were not successful.
7 citations
TL;DR: The isolated 3′-deoxyglycal nucleoside was characterized by X-ray and NMR spectral analyses and afforded 3- deoxy-3-(4-methoxypyrimidin-2-on-1-y1)glycal as the major product in a stereoselective manner.
Abstract: The intramolecular glycosylation of a 6-O-(4-methoxypyrimidin-2-yl) derivative of phenyl 2,3-didehydrohex-2-eno-1-thiopyranoside afforded 3-deoxy-3-(4-methoxypyrimidin-2-on-1-y1)glycal as the major product in a stereoselective manner. The isolated 3′-deoxyglycal nucleoside was characterized by X-ray and NMR spectral analyses.
7 citations
TL;DR: In this article, the base-catalysed elimination of a 4-(substituted) hydroxy group to generate a Δ4,5 pyranose is described.
7 citations
7 citations
TL;DR: Investigation into the selective deprotection of 5′-silyl versus 3′- silyl and subsequent glycosidic bond cleavage are reported herein and both modifications are required for the formation of the furanoid glycal.
Abstract: Thermolytic cleavage of 3′-OH protected thymidine is the most common method of preparing furanoid glycals. We have observed that glycosidic bond cleavage is more facile when the 5′-OH of thymidine was also protected with a silyl group. Addition of trimethylsilyl chloride facilitated cleavage of the glycosidic bond; thus, both modifications are required for the formation of the furanoid glycal. Investigations into the selective deprotection of 5′-silyl versus 3′-silyl and subsequent glycosidic bond cleavage are reported herein.
7 citations