Dimethyl Sulfoxide-Acid Anhydride Mixtures. New Reagents for Oxidation of Alcohols<sup>1</sup>

Albright, J. Donald; Goldman, Leon

doi:10.1021/ja01096a055

Cited by 298 publications

(82 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…SR-E was oxidised with DMSO in acetic anhydride [12]. SR-E methyl ester was prepared by 15 h treatment with 14% BF3 in methanol at room temperature.…”

Section: Chemical Methodsmentioning

confidence: 99%

The structure of syringomycins A₁, E and G

Segre

Bachmann

Ballio³

et al. 1989

FEBS Letters

159

View full text Add to dashboard Cite

By a combination of 1D and 2D 1H-and ~3C-NMR, FAB-MS, and chemical and enzymatic reactions carried out at the milligram level, it has been demonstrated that syringomycin E, the major phytotoxic antibiotic produced by Pseudomonas syringae pv. syringae, is a new lipodepsipcptide. Its amino acid sequence is Ser-Ser-Dab-Dab-Arg-Phe-Dhb-4(Cl)Thr-3(OH)Asp with the fl-carboxy group of the C-terminal residue closing a macrocyclic ring on the OH group of the N-terminal Scr, which in turn is N-acylated by 3-hydroxydodecanoic acid. Syringomycins A~ and G, two other metabolites of the same bacterium, differ from syringomycin E only in their fatty acid moieties corresponding, respectively, to 3-hydroxydecanoic and 3-hydroxytetradecanoic acid.

show abstract

“…SR-E was oxidised with DMSO in acetic anhydride [12]. SR-E methyl ester was prepared by 15 h treatment with 14% BF3 in methanol at room temperature.…”

Section: Chemical Methodsmentioning

confidence: 99%

The structure of syringomycins A₁, E and G

Segre

Bachmann

Ballio³

et al. 1989

FEBS Letters

159

View full text Add to dashboard Cite

show abstract

“…The 3-2H derivative of 2-acetamido-2-deoxy-D-glucose was prepared by the initial oxidation of benzyl 3acetamido-4,6-0-benzylidene-2-deoxy-P-D-glucopyranoside (5) using dimethylsulfoxide and acetic anhydride (12). This oxidation gave almost quantitative yields of benzyl 2-acetamido-4,6-0-benzylidene-2-deoxy-P-D-ribo-hexopyranosid-3-ulose (8).…”

Section: Synthesismentioning

confidence: 99%

“…Compound 5 was acetylated at C-3 and the benzylidene group was removed by selective acidic hydrolysis to give crystalline 3. Compound 3 was tritylated at C-6 to yield crystalline benzyl 2-acetamido-3-O-acetyl-6-0-trityl-2-deoxy-P-D-glucopyranoside (4) which was oxidized using dimethylsulfoxide -acetic anhydride (12) to give excellent yields of benzyl 2-acetamido-3-0-acetyl-6-0-trityl-2-deoxy-P-D-xylo-hexopyranosid-4-ulose (7). The 4-ketone (7) was reduced with sodium borodeuteride, deacetylated, and detritylated.…”

Section: Synthesismentioning

confidence: 99%

The Carbon-13 Nuclear Magnetic Resonance Spectra of 2-Acetamido-2-deoxy-D-hexoses and some Specifically Deuteriated, O-Acetylated, and Phosphorylated Derivatives

Bundle¹,

Jennings²,

Smith³

1973

Can. J. Chem.

150

View full text Add to dashboard Cite

The 13C n.m.r. spectra of the 2-acetamido-2-deoxy-D-hexoses and some 3-0-acetyl and 1-phosphate derivatives are assigned and discussed. T o facilitate the interpretation of the spectra, an initial assignment of the resonances in the spectrum of 2-acetamido-2-deoxy-D-glucose was required. For this purpose, both the 3-2H and 4-2H derivatives of this acetamido-hexose were synthesized. These syntheses are reported together with those of 2-acetamido-3-0-acetyl-2-deoxy-D-glucose and 2-acetamido-2-deoxy a-and B-D-glucose-1-phosphate. These model compounds were used to study substituent effects related to the 2-acetamido-2-deoxy-D-hexose-containing polysaccharide antigens of N. tnet~ingitidis.On explique et on discute des spectres r.m.n. du 13C d'acetamido-2 dtoxy-2 D-hexoses et d e quelques derives 0-acttyle-3 et phosphate-1. Afin de faciliter I'interpretation des spectres, une attribution initiale des resonances dans le spectre de !'acetamido-2 deoxy-2 D-glucose a dti &tre effectuee. Dans ce but les derives 2H-3 et 2H-3 de cet acetamido hexose ont tous deux ete synthktises. Ces syntheses sont rapportkes ainsi que celles de I'acttamido-2 0-acktyle-3 deoxy-2 D-glucose et de l'acttamido-2 dkoxy-2 cr-et B-D-glucose phosphate-1. Ces composts modeles ont it6 utilists afin d'etudier les effets des substituants relies au polysaccharide antigkne de la N. rnenirtgitidis contenant I'acttamido-2 dtoxy-2 D-hexose.

show abstract

“…The structures of the 1,2,3-tris (phenylhydrazono) derivatives of cyclohexane, cyclopentane (7)* and cyclohexanecarboxylic acid were also studied. Methyl sulfoxide in acetic anhydride has proved to be an efficient reagent for the oxidation of an isolated or sterically hindered secondary alcoholic group to a ketone group in steroids [26] and partially substituted carbohydrates [27].…”

Section: Comparison Of Commercial Anthracenesmentioning

confidence: 99%

Organic chemistry:

Schaffer¹

1967

View full text Add to dashboard Cite

Dimethyl Sulfoxide-Acid Anhydride Mixtures. New Reagents for Oxidation of Alcohols¹

Cited by 298 publications

References 1 publication

The structure of syringomycins A₁, E and G

The structure of syringomycins A₁, E and G

The Carbon-13 Nuclear Magnetic Resonance Spectra of 2-Acetamido-2-deoxy-D-hexoses and some Specifically Deuteriated, O-Acetylated, and Phosphorylated Derivatives

Organic chemistry:

Contact Info

Product

Resources

About

Dimethyl Sulfoxide-Acid Anhydride Mixtures. New Reagents for Oxidation of Alcohols1

Cited by 298 publications

References 1 publication

The structure of syringomycins A1, E and G

The structure of syringomycins A1, E and G

The Carbon-13 Nuclear Magnetic Resonance Spectra of 2-Acetamido-2-deoxy-D-hexoses and some Specifically Deuteriated, O-Acetylated, and Phosphorylated Derivatives

Organic chemistry:

Contact Info

Product

Resources

About

Dimethyl Sulfoxide-Acid Anhydride Mixtures. New Reagents for Oxidation of Alcohols¹

The structure of syringomycins A₁, E and G

The structure of syringomycins A₁, E and G