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: This sequence provides models for the rapid access to intermediates for pluramycin synthesis by converts protected glycal‐substituted quinols to aryl bis C‐glycals in which one or both of the substituents is an aminoglycal.
8 citations
TL;DR: In this paper, the electrochemical bromination of 3,4,6-tri-O-acetyl-d -glucal has been investigated in DMSO by cyclic voltammetry and preparative-scale electrolyses.
8 citations
TL;DR: Daunosamine has been coupled alpha-L-glycosidically to the 3- and 4-mono-O-acetyl derivatives of L-rhamnal to afford disaccharide glycal derivatives, whose conversion into the corresponding 2-deoxyglycosides by sequential alkoxyiodination-tributylstannane reduction has been evaluated.
Abstract: Daunosamine, as its 4-O-acetyl-3-N-trifluoroacetyl glycosyl chloride derivative (1b), has been coupled α-L-glycosidically to the 3- and 4-mono-O-acetyl derivatives of L-rhamnal to afford disaccharide glycal derivatives, whose conversion into the corresponding 2-deoxyglycosides by sequential alkoxyiodination-tributylstannane reduction has been evaluated. The sequence successfully demonstrated with the methyl glycosides was successfully extended with daunomycinone as the aglycon, providing a preparative route to 7-O-[3-O-(3-amino-2, 3, 6-trideoxy-α-L-lyxo-hexopyranosyl)-2, 6-dideoxy-α-L-arabino-hexopyranosyl]daunomycinone hydrochloride (15), an analogue of natural anthracycline antibiotics containing daunosamine and a 2, 6-dideoxy-L-hexose.
8 citations
TL;DR: A mild, catalytic, and efficient protocol has been developed for the synthesis of 2,3-unsaturated glycosides or ‘pseudo-glycals’ using Zn(OTf)2 using various acceptors including alcohols, phenols, thiols, and sugar aglycones.
Abstract: A mild, catalytic, and efficient protocol has been developed for the synthesis of 2,3-unsaturated glycosides or ‘pseudo-glycals’ using Zn(OTf)2. Stereoselective glycosylation of glycal donor with various acceptors comprising of alcohols, phenols, thiols, and sugar aglycones proceeds smoothly to afford the corresponding 2,3-unsaturaed glycosides in good to excellent yields.
8 citations
TL;DR: Upon treatment with the K- and Li-enolates of a methylene active compound, such as dimethyl malonate and dibenzoylmethane, D-allal- and D-galactal-derived vinyl N-mesyl aziridines are stereoselectively transformed into diastereoisomeric, highly functionalized, enantiopure cis-2,5-disubstituted N- Mesyl- 2,5
8 citations