Studies on Aryl H-Phosphonates; Part 2: A General Method for the Preparation of Alkyl H-Phosphonate Monoesters

Kers, Annika; Kers, Inger; Stawiński, Jacek; Sobkowski, Michał; Kraszewski, Adam

doi:10.1055/s-1995-3919

Cited by 35 publications

(15 citation statements)

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“…undergo fast transesterification with alcohols in pyridine to afford mixtures of the corresponding dialkyl and alkyl phenyl H-phosphonate [12]. Inspired by this observation, a new approach to symmetrical disaccharide H-phosphonate diesters was investigated (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

A facile approach to phosphonic acid diesters

Xiao

Zhao

2003

Heteroatom Chemistry

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Section: Resultsmentioning

confidence: 99%

A facile approach to phosphonic acid diesters

Xiao

Zhao

2003

Heteroatom Chemistry

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“…N-(Methoxyphenoxyphosphanyl)glycine Methyl Ester: Title compound was synthesized according to a literature method. [38,39] Diphenyl phosphite (2 mmol) and a catalytic amounts of Et 3 N (about 5 drops) were dissolved in dry THF (5 mL) and cooled to -5°C. Under an argon atmosphere, CH 3 OH (1 mmol) in dry THF (5 mL) was added dropwise to the solution.…”

Section: Bis(9-uorenylmethyl) Phosphitementioning

confidence: 99%

On the Electrophilicity of Cyclic Acylphosphoramidates (CAPAs) Postulated as Intermediates

Gao

Zhao

et al. 2009

Eur J Org Chem

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Cyclic acylphosphoramidates (2-hydroxy-2-oxy-1,3,2-oxazaphospholidine-5-ones, CAPAs) are phosphate-activated amino acids possessing both a carboxyl-phosphoryl anhydride and a phosphoramidate bond in a ring. They structurally resemble NCAs (amino acid N-carboxyanhydrides, Leuchs' anhydrides), which have been extensively investigated. By contrast, the chemistry of CAPAs has remained almost unexplored since it was proposed in a prebiotic reaction of inorganic polyphosphates (Polyps) with amino acids. In the present work, the bielectrophilicity of alpha-CAPAs (Gly-CAPA, Ala-CAPA) was identified by isotopic analysis (O-18, N-15) and further proved by trapping alpha-CAPA with nucleophiles such as water, amino acids, phosphate and methanol in alkaline media, which yielded N-phosphoamino acids and peptide phosphoanhydride and phosphate ester derivatives. By comparison with the reactivity of NCAs, the bielectrophilicity of CAPAs indicates that CAPAs can provide rich chemistry. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weiriheim, Germany, 2009)Ministry of Science and Technology [2006DFA43030]; Chinese National Natural Science Foundation [20732004

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“…During our studies on transesterification of diphenyl H-phosphonate (1, DPP) with various alcohols [9], we observed that even the sterically hindered tertbutanol efficiently replaced a phenoxy group in 1 to produce tert-butyl phenyl H-phosphonate. This, upon hydrolysis, afforded tert-butyl H-phosphonate monoester in 91% overall yield.…”

Section: Reaction Of Tritanol With Diphenyl Hphosphonate In Pyridinementioning

confidence: 99%

Studies on the reaction of trityl derivatives withH-phosphonate diesters: Their relevance to the synthesis of 4-pyridylphosphonates

et al. 1999

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Studies on Aryl H-Phosphonates; Part 2: A General Method for the Preparation of Alkyl H-Phosphonate Monoesters

Cited by 35 publications

References 0 publications

A facile approach to phosphonic acid diesters

A facile approach to phosphonic acid diesters

On the Electrophilicity of Cyclic Acylphosphoramidates (CAPAs) Postulated as Intermediates

Studies on the reaction of trityl derivatives withH-phosphonate diesters: Their relevance to the synthesis of 4-pyridylphosphonates

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