Glycosyl trifluoroacetimidates. Part 1: Preparation and application as new glycosyl donors

Yu, Biao; Tao, Houchao

doi:10.1016/s0040-4039(01)00157-5

Cited by 339 publications

(202 citation statements)

References 14 publications

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“…Yu and Tao [150] and Iadonisi and co-workers [151] explored the application of O-glycosyl N-phenyltrifluoroacetimidates and reported particularly good reactivity for some specific glycosylation reactions. On the whole, trifluoroacetimidate donors are less reactive than the corresponding trichloroacetimidate donors, presumably as a result of the lower basicity of the nitrogen atom, the presence of a substituent on the nitrogen atom, and/or the smaller conformational changes caused by the trifluoromethyl group.…”

Section: O-glycosyl Imidates With Electron-withdrawing Groupsmentioning

confidence: 99%

New Principles for Glycoside‐Bond Formation

2009

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Increased understanding of the important roles that oligosaccharides and glycoconjugates play in biological processes has led to a demand for significant amounts of these materials for biological, medicinal, and pharmacological studies. Therefore, tremendous effort has been made to develop new procedures for the synthesis of glycosides, whereby the main focus is often the formation of the glycosidic bonds. Accordingly, quite a few review articles have been published over the past few years on glycoside synthesis; however, most are confined to either a specific type of glycoside or a specific strategy for glycoside synthesis. In this Review, new principles for the formation of glycoside bonds are discussed. Developments, mainly in the last ten years, that have led to significant advances in oligosaccharide and glycoconjugate synthesis have been compiled and are evaluated.

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Section: O-glycosyl Imidates With Electron-withdrawing Groupsmentioning

confidence: 99%

New Principles for Glycoside‐Bond Formation

2009

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“…Chemo-selectively removable PMB group was chosen as a protecting group at C2 position and electron-withdrawing acetyl groups at C3 and C4 were incorporated to suppress the armed feature by the PMB group, which could lead to stabilization of the donor. Furthermore, a more stable N-phenyltrifluoroacetimidate group compared to a trichloroacetimidate group was used as a leaving group [40,41]. The glycosylation of 11 with 12, which was derived from a known fucose derivative [42] and was promoted by TMSOTf in a mixed solvent system of cyclopentylmethyl ether (CPME)-dichloromethane (1:1) [43] at −80 °C, provided trisaccharide 13.…”

Section: Scheme 1 Retrosynthetic Analysis Of Target Compoundsmentioning

confidence: 99%

A New Chemical Approach to Human ABO Histo-Blood Group Type 2 Antigens

et al. 2013

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Abstract:A new chemical approach to synthesizing human ABO histo-blood type 2 antigenic determinants was developed. N-Phthaloyl-protected lactosaminyl thioglycoside derived from lactulose via the Heyns rearrangement was employed to obtain a type 2 core disaccharide. Use of this scheme lowered the overall number of reaction steps. Stereoselective construction of the α-galactosaminide/galactoside found in A-and B-antigens, respectively, was achieved by using a unique di-tert-butylsilylene-directed α-glycosylation method. The proposed synthetic scheme provides an alternative to existing procedures for preparing ABO blood group antigens.

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“…8,9) Recent studies have shown that they have cytotoxic properties against several strains of human cancer cells. [10][11][12][13][14] Dioscin [15][16][17] and trillin 18) are the best known diosgenyl saponins with these properties (Fig. 1).…”

mentioning

confidence: 99%

The Mitotic-Arresting and Apoptosis-Inducing Effects of Diosgenyl Saponins on Human Leukemia Cell Lines

Liu

Wang

et al. 2004

Biological & Pharmaceutical Bulletin

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Diosgenyl saponins are the most abundant steroid saponins, and exert a large variety of biological functions. In a previous report, we showed that dioscin was able to induce cytotoxicity and apoptosis in human myeloblast leukemia HL-60 cells. This study further investigated the action mechanisms underlying this effect. The activation of caspase-9 and -3, but not caspase-8, together with the down-regulation of anti-apoptotic Bcl-2 protein, demonstrated that the apoptotic signaling triggered by dioscin was mediated through the intrinsic mitochondriadependent pathway. We also investigated its anti-proliferative effect on human chronic myelogenous leukemia K562 cells. Flow cytometry analysis showed that dioscin treatment induced the accumulation of cells in the G 2 /M phase. Cytomorphology with DAPI and Wright-Giemsa staining demonstrated the enlargement of cell volume and multinucleation in the treated cells. Subsequent apoptosis was delineated with phosphatidylserine externalization and DNA hypodiploidy. Trillin was one of the hydrolysates of dioscin. We demonstrated that it could induce multinucleation in HL-60, K562 and human promyelocytic leukemia NB 4 cells, suggesting its extensive mitotic-arresting effects. As the diosgenyl sapogenin, diosgenin was also shown to be able to induce multinucleation and apoptosis in K562 cells in a similar manner to dioscin. These findings suggest that diosgenyl saponins have the properties to induce mitotic arrest and apoptosis, suggesting that they may be a new kind of antimitotic agent.

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Glycosyl trifluoroacetimidates. Part 1: Preparation and application as new glycosyl donors

Cited by 339 publications

References 14 publications

New Principles for Glycoside‐Bond Formation

New Principles for Glycoside‐Bond Formation

A New Chemical Approach to Human ABO Histo-Blood Group Type 2 Antigens

The Mitotic-Arresting and Apoptosis-Inducing Effects of Diosgenyl Saponins on Human Leukemia Cell Lines

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