2014
DOI: 10.1016/j.carres.2014.08.003
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Efficient synthesis of the tetrasaccharide repeating unit of the O-antigen of Escherichia coli O174 strain

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Cited by 5 publications
(3 citation statements)
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“…In all the glycosylations, only one stereoisomer of the glycosides formed were reported, either obtained as 1,2- trans -glycosides by neighboring group participation or as 1,2- cis -glycosides by solvent effects in 1:1 Et 2 O/CH 2 Cl 2 . This method has since been used in the synthesis of a wide range of natural products by the Misra group and Mandal , to selectively obtain the axial glycosidic bonds as the only stereoisomer in all the above-mentioned examples, seemingly only requiring changes in the ratio of the Et 2 O/CH 2 Cl 2 solvent mixture. The formation of the undesired 1,2- trans -glycoside was reported as a 5% byproduct in two cases. , Thus, NOBF 4 appears to be an robust catalyst for axial glycosidic bond-formation in ethereal solvents but is yet to be utilized by other research groups.…”
Section: Glycosyl Imidate Donorsmentioning
confidence: 99%
“…In all the glycosylations, only one stereoisomer of the glycosides formed were reported, either obtained as 1,2- trans -glycosides by neighboring group participation or as 1,2- cis -glycosides by solvent effects in 1:1 Et 2 O/CH 2 Cl 2 . This method has since been used in the synthesis of a wide range of natural products by the Misra group and Mandal , to selectively obtain the axial glycosidic bonds as the only stereoisomer in all the above-mentioned examples, seemingly only requiring changes in the ratio of the Et 2 O/CH 2 Cl 2 solvent mixture. The formation of the undesired 1,2- trans -glycoside was reported as a 5% byproduct in two cases. , Thus, NOBF 4 appears to be an robust catalyst for axial glycosidic bond-formation in ethereal solvents but is yet to be utilized by other research groups.…”
Section: Glycosyl Imidate Donorsmentioning
confidence: 99%
“…Found: C, 47.73; H, 6.54. C 14 To a suspension of compound 4 (2 g, 2.16 mmol) in acetic anhydride (10 mL) was added HClO 4 /SiO 2 (150 mg) and the reaction mixture was allowed to stir at room temperature for 30 min. The solvents were removed under reduced pressure and co-evaporated using toluene (3Â50 mL).…”
Section: Ethyl 246-tri-o-acetyl-1-thio-a-d-mannopyranoside (3)mentioning
confidence: 99%
“…The NOE based NMR spectral analysis in conjugation with molecular dynamics (MD) simulation techniques provides insight of the conformational behavior of the molecules. 13 As a part of the ongoing program on the synthesis of complex oligosaccharides and their conformational studies, 14 synthesis of a pentasaccharide repeating unit of the cell wall Oantigen of the E. coli O175 as its 2-(p-methoxyphenoxy) ethyl glycoside using one-pot, three components [1þ2þ2] block glycosylation and its conformational analysis using 2D ROESY NMR spectral analysis and MD simulation technique are presented herein. The use of 2-(p-methoxyphenoxy) ethyl group as the anomeric protecting group would provide the molecule with a readily available ethylene glycol linker attached to it.…”
Section: Introductionmentioning
confidence: 99%