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 showed that 3,7-anhydro-4,5,6,8-tetra-O -benzyl-1,2-dideoxy-d- glycero-d - galacto- oct-3-en-1-ynitol (glycal acetylene, 3 ) is the major product.
Abstract: Treatment of 3,7-anhydro-4,5,6,8-tetra- O -benzyl-1,2-dideoxy- d - glycero - d - galacto- oct-1-ynitol (β- d -mannosyl acetylene, 1 ) with 5 equivalents of n -butyllithium at either 0 or −78 °C resulted in the elimination of benzyl alcohol to yield 3,7-anhydro-5,6,8-tri- O -benzyl-1,2,4-trideoxy- d - arabino- oct-3-en-1-ynitol (glycal acetylene, 3 ) as the major product. Additional studies showed that 3 is also produced from two isomers of 1 with α- d -mannosyl and β- d -glucosyl stereochemistry, but in lower yields. Furthermore, substrates in which the acetylene moiety is replaced by either a methyl or phenyl group do not produce a glycal product under these conditions. Finally, treatment of 1 with phenyllithium provides 3 in low yield. Deuterium labeling studies suggest that the reaction proceeds through an E2, rather than an E1cB, mechanism.
TL;DR: 2-Deoxy-2-iodo-N-glycosylamides have been prepared in high yields and with good selectivities by a one step process starting from glycals by tin hydride mediated reductive deiodination.
Abstract: 2-Deoxy-2-iodo-N-glycosylamides have been prepared in high yields and with good selectivities by a one step process starting from glycals. The resulting trans-configured 2-deoxy-2-iodo-N-glycosylamides are readily converted to the 2-deoxy-N-glycosylamides by tin hydride mediated reductive deiodination. Aliphatic and aromatic primary amides, substituted ureas and amino acids were added to glycals in this fashion. The stereoselectivity and yields in these reactions were governed by a variety of factors including the nature of the solvent used in the addition reaction, the types of protecting groups on the glycal, and the nature of the R group on the amide.
TL;DR: CMP-3-fluoroneuraminic acid, a useful mechanistic probe for sialyltransferases, has been efficiently synthesized using recent fluorination and phosphorylation techniques from a sialic acid glycal as discussed by the authors.
Abstract: CMP-3-fluoroneuraminic acid, a useful mechanistic probe for sialyltransferases, has been efficiently synthesized using recent fluorination and phosphorylation techniques from a sialic acid glycal.
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 mentioned in this paper.
Abstract: Amberlyst 15 serves as an inexpensive, effective, and environmentally friendly catalyst in converting 3,4,6‐tri‐O‐acetyl‐D‐glucal (1) into 2,3‐unsaturated O‐ and S‐glycosides via Ferrier rearrangement in moderate to excellent yields with high α selectivity.
TL;DR: In this paper, a catalytic cycle was developed for the conversion of glycosyl halides to their corresponding glycals using Cp2TiCl2, which can be effectively used with only 30% of the in situ generated single electron reducing agent in contrast to the 2 equivalents normally employed.
Abstract: A catalytic cycle has been developed for the conversion of glycosyl halides to their corresponding glycals using Cp2TiCl2. This process can be effectively used with only 30% of the in situ generated single electron reducing agent in contrast to the 2 equivalents normally employed.