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 paper deals with new approaches to alpha-Neu5NAc-(2,6)-D-GalN3 building blocks, suitable as glycosylation donors, and develops a new tert-butyldimethylsilyl disaccharide that can be transformed into a donor, after cleavage of the anomeric group in smooth conditions.
12 citations
TL;DR: The pyranose members of the pyrrolomorpholine spiroketal family have been synthesized by stereoselective spirocyclizations of a common glycal precursor, leading to the identification of novel 2-hydroxy analogues with more potent antioxidant activities than the natural products.
Abstract: The pyranose spiroketal natural products pollenopyrroside A and shensongine A (also known as xylapyrroside A, ent-capparisine B) have been synthesized by stereoselective spirocyclizations of a common C1-functionalized glycal precursor. In conjunction with our previously reported syntheses of the corresponding furanose isomers, this provides a versatile family-level synthesis of the pyrrolomorpholine spiroketal natural products and analogues. In rat mesangial cells, hyperglycemia-induced production of reactive oxygen species, which is implicated in diabetic nephropathy, was inhibited by pollenopyrroside A and shensongine A with mid-μM IC50 values, while unnatural C2-hydroxy analogues exhibited more potent, sub-μM activity.
12 citations
TL;DR: A highly efficient and mild method for the synthesis of glycosyl sulfonamides andglycosyl amides from glycal has been described using Zn(OTf)2 as an economical and environmentally friendly catalyst.
11 citations
Abstract: Analogs of the C-nucleoside pyrazofurin were prepared in 7–9 steps using a key Pd(0)- catalyzed coupling reaction between protected iodopyrazoles 6a and 6b and glycal 8 to form the glycosyl bond. Conditions for this reaction were improved from those previously described for related reactions in order to maximize product yields and eliminate the need for triphenylarsine. † present address: Arris Pharmaceutical, 385 Oyster Point Blvd., South San Francisco, CA 94080
11 citations
TL;DR: Amberlyst 15 serves as an inexpensive, effective, and environmentally friendly catalyst in converting 3,4,6,tri-O-acetyl-D-glucal into 2,3,unsaturated O and S-glycosides via Ferrier rearrangement in moderate to excellent yields with high α selectivity as discussed by the authors.
11 citations