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Glycal

About: Glycal is a(n) research topic. Over the lifetime, 897 publication(s) have been published within this topic receiving 17422 citation(s).

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Journal ArticleDOI
01 Jul 1996-Angewandte Chemie
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.

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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.

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576 citations


Journal ArticleDOI
28 May 1993-Science
TL;DR: Repeating glycosidic linkages of oligosaccharides can be synthesized by solid-phase methods using glycals attached to a polystyrene copolymer with a silyl ether bond.

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Abstract: Repeating glycosidic linkages of oligosaccharides can be synthesized by solid-phase methods. Glycals were attached to a polystyrene copolymer with a silyl ether bond and were activated to function as glycosyl donors with 3,3-dimethyldioxirane. Glycosidation was performed by reactions with a solution-based acceptor (itself a glycal). Excess acceptor and promoter were removed by rinsing after each coupling, and the desired oligosaccharides were then easily obtained from the polymer by the addition of tetra-n-butylammonium fluoride. By this method, glycosidations are stereospecific and interior deletions are avoided.

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269 citations


Journal ArticleDOI
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

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185 citations


Journal ArticleDOI
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.

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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.

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168 citations


Journal ArticleDOI
Abstract: Synthese d'oligosaccharides a partir de tri-O-benzyl-3,4,6 glucal, de di-O-benzoyl-3,4 glucal et d'hexofuranoses ou d'hexopyranoses proteges

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149 citations


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Performance
Metrics
No. of papers in the topic in previous years
YearPapers
202111
202011
20197
201819
201717
201611

Top Attributes

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Topic's top 5 most impactful authors

Samuel J. Danishefsky

24 papers, 1.5K citations

Valeria Di Bussolo

17 papers, 247 citations

Hiromichi Tanaka

10 papers, 97 citations

Xue-Wei Liu

10 papers, 159 citations

Samuel J. Danishefsky

9 papers, 466 citations