Synthesis of 1-O-methyl-.beta.,D-ezoaminuroic acid

Knapp, Spencer; Levorse, Anthony T.; Potenza, Joseph A.

doi:10.1021/jo00255a020

Cited by 28 publications

(8 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The title compound was prepared on a 2.0 mmol scale from 20c according to the procedure given for 23a. Direct inlet MS (EI) m/z (relative intensity): 392 (M + +2, 1.7), 390 (M + , 5.8), 171 (11), 169 (37), 149 (71), 105 (17), 91 (24), 59 (100).…”

Section: -Methyl-3-[2-(2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)ethoxy)...mentioning

confidence: 99%

“…500 3-[(3-iso-Butoxy-2-methyl)benzoyl]propionic Acid (27a). 37 Compound 26a (2.11 g, 6.27 mmol) was dissolved in EtOH-H2O (4:1, 10 mL) and treated with NaOH (2M, 5 mL) at ambient temperature for 24 h. The mixture was acidified with HCl (6 M), and the solvents were evaporated. The residue was partitioned between Et 2O and HCl (1 M).…”

Section: -Methyl-3-[2-(morpholino)ethoxy]benzyl Chloride Hydrochlorid...mentioning

confidence: 99%

“…100 MHz 13 C NMR (CH3-OH-d4): δ 14.4, 62.12, 125.85, 127.38, 129.10, 135.58, 136.05, 140.24. Direct inlet MS (EI) for C8H10OS m/z (relative intensity): 154 (M + , 100), 137 (51), 136 (92), 135 (53), 121 (38), 92 (37), 91 (90), 77 (43).…”

Section: -Methyl-3-mercapto-benzyl Alcohol (31)mentioning

confidence: 99%

See 2 more Smart Citations

Novel Structures Derived from 2-[[(2-Pyridyl)methyl]thio]-1H-benzimidazole as Anti-Helicobacter pylori Agents, Part 1

et al. 2002

View full text Add to dashboard Cite

2-[[(2-Pyridyl)methyl]thio]-1H-benzimidazoles (2, sulfides) exhibit antibacterial properties that are selective for Helicobacter spp., but they also have an inherent susceptibility to metabolic oxidation to furnish 2-[[(2-pyridyl)methyl]sulfinyl]-1H-benzimidazoles (1), which act as proton pump inhibitors (PPIs). We have discovered five compounds with retained antibacterial potency and selectivity in which the overall framework of the sulfides 2 could be kept intact while structural modifications were made to remove PPI activity. These compounds, 2-[((2-methyl-3-(2-(2-(2-methoxyethoxy)ethoxy)ethylthio)phenyl)methyl)thio]-1H-benzimidazole (79), 2-[((2-methyl-3-(2-(2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)ethoxy)ethylthio)phenyl)methyl)thio]-1H-benzimidazole (80), 2-[((2-methyl-3-((2-morpholino)ethylthio)phenyl)methyl)thio]-1H-benzimidazole (86), 2-[[[2-methyl-3-[2-(2-methyl-5-nitroimidazol-1-yl)ethylthio]phenyl]methyl]thio]-1H-benzimidazole (88), and 2-[[[2-methyl-3-[2-(1,2,4-triazol-1-yl)ethylthio]phenyl]methyl]thio]-1H-benzimidazole (89), had minimum bactericidal concentrations (MBCs) of 0.5, 0.5, 1, 2, and 4 microg/mL, respectively. The reported compounds are bactericidal with MBCs within 1 order of magnitude of MBCs of clinically used antimicrobials such as clarithromycin (0.1 microg/mL) or metronidazole (2-4 microg/mL) but differ from these inasmuch that they have an extremely narrow spectrum activity and appear to be species specific.

show abstract

Section: -Methyl-3-[2-(2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)ethoxy)...mentioning

confidence: 99%

Section: -Methyl-3-[2-(morpholino)ethoxy]benzyl Chloride Hydrochlorid...mentioning

confidence: 99%

See 1 more Smart Citation

Novel Structures Derived from 2-[[(2-Pyridyl)methyl]thio]-1H-benzimidazole as Anti-Helicobacter pylori Agents, Part 1

et al. 2002

View full text Add to dashboard Cite

show abstract

“…The complex structural features and antifungal potential of the ezomycins represents an attractive target for total synthesis and structure−activity relationship related studies. Although the syntheses of various structural fragments of ezomycins have been reported, , the total synthesis of this family of compounds has not yet been achieved . In continuation of our studies on complex peptidyl nucleoside antibiotics, we report herein an efficient route to a strategically protected, masked ezoaminuroic acid structural core.…”

mentioning

confidence: 99%

Stereoselective Route to the Ezoaminuroic Acid Core of the Ezomycins

Khalaf

Datta

2005

J. Org. Chem.

View full text Add to dashboard Cite

Starting from readily available (R)-glycidol, an efficient pathway to a strategically functionalized ezoaminuroic acid derivative of the antifungal ezomycins has been developed. A key transformation in the synthesis involves regio- and stereoselective conversion of the olefinic functionality of a 5,6-dihydropyran-2-one to the C-2, C-3 trans-1,2-amino alcohol moiety as present in ezoaminuroic acid.

show abstract

“…BrH2.ClO4/q;;m;-1 InChIKey = FJFPYNKGYZGNMG-AYSKBTDJCC (reactive electrophilic brominating agent; activates alkenes towards nucleophilic reagents; 2 reagent for bromocyclization, 3,4 useful in the preparation of cis-α-alkylamino alcohols)…”

mentioning

confidence: 99%

Bromonium Di-sym-collidine Perchlorate

Ray

2001

Encyclopedia of Reagents for Organic Synthesis

View full text Add to dashboard Cite

Synthesis of 1-O-methyl-.beta.,D-ezoaminuroic acid

Cited by 28 publications

References 0 publications

Novel Structures Derived from 2-[[(2-Pyridyl)methyl]thio]-1H-benzimidazole as Anti-Helicobacter pylori Agents, Part 1

Novel Structures Derived from 2-[[(2-Pyridyl)methyl]thio]-1H-benzimidazole as Anti-Helicobacter pylori Agents, Part 1

Stereoselective Route to the Ezoaminuroic Acid Core of the Ezomycins

Bromonium Di-sym-collidine Perchlorate

Contact Info

Product

Resources

About