Dialkyl (1-Hydroxyiminoalkyl)phosphonates from 1-Bromo-1-nitroalkanes and Trialkyl Phosphites

Kim, Kwan Soo; Hurh, Eun Young; Youn, Jae Nam; Park, Jong Il

doi:10.1021/jo9908344

Cited by 27 publications

(8 citation statements)

References 19 publications

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“…New or improved methods for phosphonate synthesis continue to attract much attention because phosphonates have biologically important properties and serve as natural products, analogues of phosphates, phosphonopeptides, amino acid analogues, and prodrugs. Also the phosphonate esters have physiological activity within the cell [29][30][31][32][33][34].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of aromatic amine phosphonato ester derivatives from the stereoselective reaction between triphenyl phosphite and dimethyl acetylenedicarboxylate in the presence of derivatives of aromatic amines

Maghsoodlou

Heydari

Hazeri

et al. 2009

Heteroatom Chemistry

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Section: Introductionmentioning

confidence: 99%

Synthesis of aromatic amine phosphonato ester derivatives from the stereoselective reaction between triphenyl phosphite and dimethyl acetylenedicarboxylate in the presence of derivatives of aromatic amines

Maghsoodlou

Heydari

Hazeri

et al. 2009

Heteroatom Chemistry

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“…Thus, the 1 H NMR spectrum of 6 showed two doublets for three protons at δ = 1.50 and 1.57 ppm respectively. Both signals exhibit a 3 J P,C of about 12 Hz, which is typical in the methyl groups of compounds possessing a iminoethylphosphonate structure . However, compound 6 decomposed upon standing, and the 1 H NMR spectrum also showed the presence of the methyl acetylphosphonate formed from the hydrolysis of the imino group.…”

Section: Resultsmentioning

confidence: 91%

An Improved Synthesis of the Antibiotic Dehydrophos

2018

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Within this work an efficient procedure for the synthesis of the vinyl phosphonate tripeptide dehydrophos is described. This procedure constitutes a significant improvement over previously described strategies, since critical transformations in the synthesis of dehydrophos were carried out in only two synthetic steps, with higher yields and under smooth conditions. Thus, the dehydrophosphoalanine residue was generated by means of the Horner–Wadsworth–Emmons reaction of formaldehyde with a peptide bearing an aminomethylbis(phosphonate) moiety, whereas deprotection of the N‐terminal position of the thus‐obtained dehydrophosphonopeptide and partial hydrolysis of the dimethyl phosphonate residue took place simultaneously. In addition, we confirmed that the chiral integrity of the leucine residue was preserved throughout these transformations.

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“…Tetrahalomethanes react with nucleophiles usually at the halogen with displacement of X 3 C -. Reactions of 1-halo-1-nitroalkanes with iodide [145] and with phosphorus [145,147], nitrogen [148], and carbon [149] nucleophiles. Treatment of CCl 4 or CHCl 3 with alcoholates, for instance, yields trialkyl orthoformates (HC(OR) 3 ) in both cases [150,151] (Scheme 4.37).…”

Section: Electrophiles With More Than One A-heteroatommentioning

confidence: 99%

Aliphatic Nucleophilic Substitutions: Problematic Electrophiles

Dörwald

2004

Side Reactions in Organic Synthesis

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Nucleophilic substitutions at sp 3 -hybridized carbon are among the most useful synthetic transformations, and have been thoroughly investigated [1][2][3]. The success of these reactions depends mainly on the structures of the nucleophile and electrophile, their concentration, and on the solvent and reaction temperature chosen. The structure of the electrophile in nucleophilic substitutions is of critical importance, because many unwanted side reactions result from unexpected reactivity of the electrophile.In Scheme 4.1 the mechanisms of typical monomolecular (Sn1) and bimolecular (Sn2) nucleophilic substitutions at a neutral electrophile with an anionic nucleophile are sketched. Sn1 reactions usually occur when the electrophile is sterically

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Dialkyl (1-Hydroxyiminoalkyl)phosphonates from 1-Bromo-1-nitroalkanes and Trialkyl Phosphites

Cited by 27 publications

References 19 publications

Synthesis of aromatic amine phosphonato ester derivatives from the stereoselective reaction between triphenyl phosphite and dimethyl acetylenedicarboxylate in the presence of derivatives of aromatic amines

Synthesis of aromatic amine phosphonato ester derivatives from the stereoselective reaction between triphenyl phosphite and dimethyl acetylenedicarboxylate in the presence of derivatives of aromatic amines

An Improved Synthesis of the Antibiotic Dehydrophos

Aliphatic Nucleophilic Substitutions: Problematic Electrophiles

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