29741-69-3Relevant academic research and scientific papers
A Mechanistic Probe into 1,2-cis Glycoside Formation Catalyzed by Phenanthroline and Further Expansion of Scope
Li, Jiayi,Nguyen, Hien M.
supporting information, p. 4054 - 4066 (2021/07/16)
Phenanthroline, a rigid and planar compound with two fused pyridine rings, has been used as a powerful ligand for metals and a binding agent for DNA/RNA. We discovered that phenanthroline could be used as a nucleophilic catalyst to efficiently access high
HEPARANASE INHIBITORS FOR TREATMENT OF DIABETES
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Paragraph 0302; 0311, (2021/07/10)
Anti-heparanase compounds for the treatment of diabetes are described. The anti-heparanase compounds are high affinity, synthetic glycopolymers that result in minimal anticoagulant activity. Stereoselective fluorinated forms of these compounds are also pr
HEPARANASE INHIBITORS AND THEIR USE AS ANTI-CANCER COMPOUNDS
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, (2020/07/04)
Anti-heparanase compounds for the treatment of cancer are described. The anti-heparanase compounds are high affinity, synthetic glycopolymers that result in minimal anticoagulant activity. Stereoselective fluorinated forms of these compounds are also prov
Phenanthroline-Catalyzed Stereoretentive Glycosylations
Yu, Fei,Li, Jiayi,DeMent, Paul M.,Tu, Yi-Jung,Schlegel, H. Bernhard,Nguyen, Hien M.
, p. 6957 - 6961 (2019/04/17)
Carbohydrates are essential moieties of many bioactive molecules in nature. However, efforts to elucidate their modes of action are often impeded by limitations in synthetic access to well-defined oligosaccharides. Most of the current methods rely on the
Koenigs–Knorr Glycosylation Reaction Catalyzed by Trimethylsilyl Trifluoromethanesulfonate
Singh, Yashapal,Demchenko, Alexei V.
supporting information, p. 1461 - 1465 (2019/01/04)
The discovery that traditional silver(I)-oxide-promoted glycosidations of glycosyl bromides (Koenigs–Knorr reaction) can be greatly accelerated in the presence of catalytic trimethylsilyl trifluoromethanesulfonate (TMSOTf) is reported. The reaction conditions are very mild that allowed for maintaining a practically neutral pH and, at the same time, providing high rates and excellent glycosylation yields. In addition, unusual reactivity trends among a series of differentially protected glycosyl bromides were documented. In particular, benzoylated α-bromides were much more reactive than their benzylated counterparts under these conditions.
Regenerative Glycosylation
Singh, Yashapal,Wang, Tinghua,Geringer, Scott A.,Stine, Keith J.,Demchenko, Alexei V.
, p. 374 - 381 (2018/01/01)
Previously, we communicated 3,3-difluoroxindole (HOFox)-mediated glycosylations wherein 3,3-difluoro-3H-indol-2-yl (OFox) imidates were found to be key intermediates. Both the in situ synthesis from the corresponding glycosyl bromides and activation of the OFox imidates could be conducted in a regenerative fashion. Herein, we extend this study to the synthesis of various glycosidic linkages using different sugar series. The main outcome of this study relates to enhanced yields and/or reduced reaction times of glycosylations. The effect of HOFox-mediated reactions is particularly pronounced in case of unreactive glycosyl donors and/or glycosyl acceptors. A multistep regenerative synthesis of oligosaccharides is also reported.
Synthesis of a pentasaccharide fragmant of Polysaccharide II of Mycobacterium tuberculosis
Pozsgay, Vince,Robbins, John B.
, p. 51 - 66 (2007/10/02)
Stereocontrolled, stepwise synthesis of decyl glycosides of α-(1 -->2)-linked di- to pentaglucosides (1-5) is described; these constitute fragments of Polysaccharide II of Mycobacterium tuberculosis.Phenyl 3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-?-D-glucopyranoside (7) was used as the single key intermediate, obtained from 1,3,4,6-tetra-O-acetyl-2-O-benzyl-β-D-glucopyranose (6) and PhSSiMe3.Halogenolysis of 7 afforded the isolated β bromide (10) and β chloride (13).Solvolysis of 10 with decanol without heavy metal salts gave decyl 3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glucopyranoside (14) in a highly stereoselective reaction, in high yield.Subsequent, iterative hydrogenolytic removal of the O-benzyl group and glycosylation with the β-chloride 13 under catalysis by silver salts afforded the protected di- to penta-saccharide glycosides 16, 19, 21, and 23, which were conventionally deblocked.Keywords: Pentasaccharide; Polysaccharide II; Mycobacterium tuberculosis
STEREOCHEMICAL VARIATIONS IN AQUEOUS CYCLOADDITIONS USING GLYCO-ORGANIC SUBSTRATES AS A CONSEQUENCE OF CHEMICAL MANIPULATIONS ON THE SUGAR MOIETY
Lubineau, Andre,Queneau, Yves
, p. 6697 - 6712 (2007/10/02)
Chemical modifications of the sugar moiety in dienyl glycosides allowed us to rationalize the stereochemistry of our aqueous cycloadditions using glyco-organic substrates.In this way, several dienyl glucosides having benzyl group in 2 or 6 position of the
