Topic
Glycal
About: Glycal is a research topic. Over the lifetime, 897 publications have been published within this topic receiving 17422 citations.
Papers published on a yearly basis
1 / 2
Papers
TL;DR: This review provides a personal account of the explorations of a research group in oligosaccharide and glycoconjugate construction that led to novel compounds which are in the final stages of preclinical assessment.
Abstract: This review provides a personal account of the explorations of a research group in oligosaccharide and glycoconjugate construction. The journey began twenty years ago with the study of Diels–Alder reactions of complex dienes. By extending this methodology to aldehydo-type heterodienophile equivalents, access to unnatural glycals was gained (LACDAC reaction). From this point a broad-ranging investigation of the use of glycals in the synthesis of oligosaccharides and other glycoconjugates was begun. Mobilization of glycals both as glycosyl donors and glycosyl acceptors led to the strategy of glycal assembly. Several new glycosylation techniques were developed to provide practical underpinning for this logic of glycal assembly. Glycal-based paradigms have been shown to be nicely adaptable to solid phase supported synthesis. Moreover, glycal assembly—both in solution and on solid phases—has been used to gain relatively concise and efficient entry to a variety of biologically interesting and potentially valuable constructs. Some of these syntheses, particularly in the field of tumor antigens, have led to novel compounds which are in the final stages of preclinical assessment. This review presents an account of the chemical reasoning at the center of the program.
645 citations
TL;DR: A review of the explorations of a research group in oligosaccharide and glycoconjugate construction can be found in this article, where the authors present an account of the chemical reasoning at the center of the program.
Abstract: This review provides a personal account of the explorations of a research group in oligosaccharide and glycoconjugate construction. The journey began twenty years ago with the study of Diels–Alder reactions of complex dienes. By extending this methodology to aldehydo-type heterodienophile equivalents, access to unnatural glycals was gained (LACDAC reaction). From this point a broad-ranging investigation of the use of glycals in the synthesis of oligosaccharides and other glycoconjugates was begun. Mobilization of glycals both as glycosyl donors and glycosyl acceptors led to the strategy of glycal assembly. Several new glycosylation techniques were developed to provide practical underpinning for this logic of glycal assembly. Glycal-based paradigms have been shown to be nicely adaptable to solid phase supported synthesis. Moreover, glycal assembly—both in solution and on solid phases—has been used to gain relatively concise and efficient entry to a variety of biologically interesting and potentially valuable constructs. Some of these syntheses, particularly in the field of tumor antigens, have led to novel compounds which are in the final stages of preclinical assessment. This review presents an account of the chemical reasoning at the center of the program.
318 citations
TL;DR: Photolysis of 0.25 equiv of W(CO)6 in the presence of tertiary amines and highly functionalized terminal alkynyl alcohols catalyzes single-step, high-yield cycloisomerization to endocyclic enol ethers, leading to enantio- and diastereoselective syntheses of each isomer of 6-deoxy-1,2-glycals.
Abstract: Photolysis of 0.25 equiv of W(CO)6 in the presence of tertiary amines (triethylamine or DABCO) and highly functionalized terminal alkynyl alcohols catalyzes single-step, high-yield cycloisomerization to endocyclic enol ethers. This transformation is general for each diastereomeric 3,4-bissilyl ether of 5-hydroxy-1-hexyne, leading to enantio- and diastereoselective syntheses of each isomer of 6-deoxy-1,2-glycals. Stereoselective glycosylations have also been demonstrated for each glycal diastereomer, and have been applied in the preparation of d-digitoxose-β-4-d-digitoxose glycal.
207 citations
TL;DR: In this paper, an efficient catalytic procedure for the preparation of 2-deoxyglucosides from glucals without allylic or Ferrier rearrangement using triphenylphosphine hydrobromide and a wide variety of hydroxylic nucleophiles is described.
Abstract: An efficient catalytic procedure for the preparation of 2-deoxyglucosides from glucals without allylic or Ferrier rearrangement using triphenylphosphine hydrobromide and a wide variety of hydroxylic nucleophiles is described
196 citations
TL;DR: Methods for the preparation of C-aryl glycosides, and their application to the total synthesis of naturally occurring C -aryl glycolysisides, are reviewed in this article.
Abstract: Methods for the preparation of C-aryl glycosides, and their application to the total synthesis of naturally occurring C-aryl glycosides, are reviewed
187 citations
Related Topics (5)
Performance Metrics
| Year | Papers |
|---|---|
| 2025 | 14 |
| 2024 | 9 |
| 2023 | 15 |
| 2022 | 11 |
| 2021 | 11 |
| 2020 | 11 |