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  • 1
    Electronic Resource
    Electronic Resource
    Biosynthesis of natural products with a phosphorus-carbon bond. 7. Synthesis of [1,1-2H2]-, [2,2-2H2]-, (R)- and (S)-[1-2H1](2-hydroxyethyl)phosphonic acid and (R,S)-[1-2H1](1,2-dihydroxyethyl)phosphonic acid and incorporation studies into fosfomycin in Streptomyces fradiae (1991)
    s.l. : American Chemical Society
    The @journal of organic chemistry 56 (1991), S. 2364-2370 
    Details
    ISSN: 1520-6904
    Source: ACS Legacy Archives
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1021/jo00007a022
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  • 2
    Electronic Resource
    Electronic Resource
    ZumHunsdiecker-Abbau von 2-Acylcyclopropancarbonsäuren (1977)
    Springer
    Monatshefte für Chemie 108 (1977), S. 1253-1263 
    Details
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract 2-Acylcyclopropane carboxylic acids (1) are degraded by aHunsdiecker reaction using red HgO/Br2 to mixtures oftrans- andcis-2-bromo-cyclopropyl alkanones, the former being the major component. The starting materials may be easily prepared by reaction of stabilised S-ylides $$(CH_3 )_2 \mathop S\limits^ \oplus \mathop C\limits^ \ominus HOOC_2 H_5 {\text{ }}and{\text{ }}(CH_3 )_2 \mathop S\limits^ \oplus \mathop C\limits^ \ominus HOOC_6 H_5 $$ with α,β-unsaturated oxo compounds or β-acylvinyltriphenylphosphonium bromides.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01046438
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  • 3
    Electronic Resource
    Electronic Resource
    Neuartige synthetische Aspekte der Phosphonat-Phosphat-Umlagerung, 2. Mitt.: Synthese von Enolphosphaten aus 1-Oxoalkanphosphonaten und Schwefelyliden (1980)
    Springer
    Monatshefte für Chemie 111 (1980), S. 1015-1023 
    Details
    ISSN: 1434-4475
    Keywords: Acylphosphonates ; behaviour towards S-ylides ; Rearrangement of α-hydroxyphosphonates
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract Acylphosphonates1 react with Sulfur-ylides2 to give enolphosphates3 and phosphonophosphates4. The product ratio of3 and4 is determined by the substituentR 3. IfR 3 is not electronwithdrawing the phosphonophosphate4 is the sole reaction product.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00909658
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  • 4
    Electronic Resource
    Electronic Resource
    Markierte Vertreter eines möglichen Zwischenprodukts der Biosynthese von Fosfomycin inStreptomyces fradiae: Darstellung von (R,S)-(2-Hydroxypropyl)-, (R,S)-, (R)-, (S)-(2-Hydroxy-[1,1-2H2]propyl)-und (R,S)-(2-[18O]Hydroxypropyl)phosphonsäure (1991)
    Springer
    Monatshefte für Chemie 122 (1991), S. 389-398 
    Details
    ISSN: 1434-4475
    Keywords: (2-Hydroxypropyl)phosphonic acids ; Deuterium-labelling of ; 18O-labelling of ; Chiral lactates
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Summary Racemic methyl O-benzyllactate was reduced to the alcohol, transformed into the bromide and reacted with triethylphosphite to give the diethylphosphonate. Removal of protecting groups afforded a phosphonic acid which was purified as its cyclohexylammonium salt. (S)-Ethyl and (R)-isobutyl O-benzyllactate were reduced with LiAlD4 to the corresponding dideuteriated alcohols, which were transformed in the same way as the racemic compound into the chiral (2-hydroxy-[1,1-2H2]propyl)phosphonic acids. The optical purity of alcohols (S)- and (R)-6 b was determined by derivatisation with (+)-MTPA-Cl and1H-NMR-spectroscopy to be 98%. Exchange of the carbonyl-16-oxygen atom of 2-oxopropylphosphonate for oxygen-18 from H2 18O, reduction with NaBH4, deprotection and addition of cyclohexylamine yielded the salt (±)-18 of (2-[18O]hydroxypropyl)phosphonic acid.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00809660
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  • 5
    Electronic Resource
    Electronic Resource
    Enzymes in Organic Chemistry VI [1]. Enantioselective Hydrolysis of 1-Chloroacetoxycycloalkylmethylphosphonates with Lipase AP 6 from Aspergillus niger and Chemoenzymatic Synthesis of Chiral, Nonracemic 1-Aminocyclohexyl- methylphosphonic Acids (1998)
    Springer
    Monatshefte für Chemie 129 (1998), S. 423-436 
    Details
    ISSN: 1434-4475
    Keywords: Keywords. α-Hydroxyphosphonates; α-Chloroacetoxyphosphonates; Enzymatic resolution; Lipase; α-Aminophosphonic acids.
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung.  Racemische α-Chloroacetoxyphosphonate, die sich von Cycloalkancarbaldehyden und drei verzweigten Aldehyden ableiten, wurden hergestellt und für die kinetische Racematspaltung mit der Lipase AP 6, die bevorzugt die (S)-Ester hydrolysiert, verwendet. Der Enantiomerenüberschuß und die Reaktionsgeschwindigkeit werden signifikant von der Ringgröe des Cycloalkylrestes beeinflußt. Die optischen Antipoden des α-Hydroxycyclohexylmethylphosphonates (3d; ee 90% bzw. ≥ 99%) wurden in die entsprechenden α-Aminophosphonsäuren 6übergeführt.
    Notes: Summary.  Racemic α-chloroacetoxyphosphonates derived from cycloalkanecarbaldehydes and three branched aldehydes were prepared and tested for kinetic resolution by lipase AP 6 which hydrolyses preferentially the (S) esters. The enantiomeric excess and the reaction rate are significantly influenced by the size of the cycloalkyl group. The optical antipodes of α- hydroxycyclohexylmethylphosphonates (3d; ee 90% and ≥99%, respectively) were transformed into the corresponding α-aminophosphonic acids 6.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/PL00000099
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  • 6
    Electronic Resource
    Electronic Resource
    Ein einfacher Weg zu D-Apio-β-D-furanosyl- und 2′-Desoxyapio-β-D-furanosylnucleosiden (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 551-558 
    Details
    ISSN: 0947-3440
    Keywords: Apionucleosides ; Nucleosides ; Antiviral agents ; Tris(trimethylsilyl)silane ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A Convenient Route to D-Apio-β-D-furanosyl- and 2′-Deoxyapio-β-D-furanosyl Nucleosides2,3-O-Isopropylidene-D-apio-β-D-furanose (1), available in 40% overall yield by modified literature procedures, is acylated regioselectively to the new 3′-O-benzoyl-derivative 2. This is converted to the anomeric triacetates 4 (β-4; α-4 = 1.8:1) by cleavage of the isopropylidene protecting group from 2 followed by peracetylation. Reaction of compounds 4 with silylated nucleobases and subsequent deprotection gives the D-apio-β-D-furanosyl nucleosides 8-10 in good yields. Regioselective hydrazinolysis of the protected nucleosides 5 and 6 affords the 2′-hydroxy-derivatives 11 and 12, respectively, which are converted to the 2′-deoxyapio-β-D-furanosyl nucleosides 17 and 18, respectively, via deoxygenation of the corresponding thionocarbonates 13 and 14 with tris(trimethylsilyl)silane and subsequent deprotection. The 2′-deoxyapio-β-D-furanosyl cytosine 20 is prepared from the 2′-deoxyapio-β-D-furanosyl uracil derivative 16.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199519950375
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  • 7
    Electronic Resource
    Electronic Resource
    Ein einfacher Weg zu 3′-Desoxy-α-L- und 3′-Desoxy-β-D-apionucleosiden (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 559-565 
    Details
    ISSN: 0947-3440
    Keywords: Apionucleosides ; Nucleosides ; Antiviral agents ; Branched nucleosides ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A Convenient Route to 3′-Deoxy-α-L- and 3′-Deoxy-β-D-apionucleosidesThe cyclic thionocarbonate 3, easily available in three steps from 3′-O-benzoyl-2,3-O-isopropylidene-D-apio-β-D-furanose (1), is deoxygenated with n-Bu3SnH to yield the 3′-deoxy epimers 4 [methyl 3-C-(benzoyloxymethyl)-3-deoxy-α-L-threo-tetrofuranoside] and 6 [methyl 3-C-(benzoyloxymethyl)-3-deoxy-β-D-erythro-tetrofuranoside]. These are separated by chromatography and further converted to the 3′-deoxy-α-L-apionucleosides 11-13, and the 3′-deoxy-β-D-apionucleosides 17-19, respectively.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199519950376
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  • 8
    Electronic Resource
    Electronic Resource
    Neuartige synthetische Aspekte der Phosphonat-Phosphat-Umlagerung, 1. Ein allgemeiner Zugang zu 1,2-Propadienylphosphaten (1980)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 113 (1980), S. 3891-3897 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Novel Synthetic Aspects of the Phosphonate-Phosphate Rearrangement, 1. An Useful Approach to 1,2-Propadienyl PhosphatesAcylphosphonates 1 react with 1-alkynes 2 in toluene to give dialkyl (1-hydroxy-2-alkynyl)phosphonates 3. These rearrange in alcohol/sodium alkoxide to 2-propynyl phosphates 4 and 1,2-propadienyl phosphates 5. Using dimethyl sulfoxide/sodium bis(trimethylsilyl)amide the compounds 5 are produced as main products.
    Notes: Aus den Acylphosphonaten 1 und den 1-Alkinen 2 werden in Toluol die Dialkyl-(1-hydroxy-2-alkinyl)phosphonate 3 synthetisiert. Diese lagern sich in Alkohol/Na-Alkoxid zu den 2-Propinyl-phosphaten 4 und den 1,2-Propadienyl-phosphaten 5 um. In Dimethylsulfoxid/Natrium-bis(trimethylsilyl)amid erhält man hauptsächlich 5.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19801131220
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  • 9
    Electronic Resource
    Electronic Resource
    Reaktionen mit phosphororganischen Verbindungen, XLIV Darstellung von 3-Oxo-1-alkenylphosphonsäure-dialkylestern (1979)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1979 (1979), S. 492-502 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Reactions with Organophosphorus Compounds, XLIV. - Synthesis of Dialkyl 3-Oxo-1-alkenylphosphonatesThe Michaelis-Arbusov reaction of 2-chlorovinyl ketones 1 with trialkyl phosphites 2 gives 2-acylvinylphosphonates 3 as well as enolphosphates 4 and 3-oxo-1,1-alkanediyldiphosphonates 5. Using the Michaelis-Becker procedure only the compounds 4 and 5 are formed as demonstrated in the case of 4d and 5d. Reaction of trimethyl and triethyl phosphite (2a and 2b) with 2-chlorovinyl ketones 1a - 1d yields mixtures of products 3a-3e, 4a-4e and 5a-5e; whereas reaction with triisopropyl phosphite (2c) gives predominantly compound 3. For example, 2c and 1a react to form a mixture consisting mainly of 2-acylvinylphosphonate 3f and a small amount of 3-oxo-1,1-alkanediyldiphosphonate 5f. Only the 2-acylvinylphosphonate 3g is isolated on reaction of 2c with 1d.
    Notes: Die Umsetzung von 2-Chlorvinylketonen 1 mit Trialkylphosphiten 2 nach Michaelis-Arbusow führt nicht nur zu den erwarteten 2-Acylvinylphosphonaten 3, sondern auch zu den Enolphosphaten 4 und zu den 3-Oxo-1,1-alkandiyldiphosphonaten 5. Bei Anwendung der Michaelis-Becker-Variante entstehen jedoch ausschließlich die Verbindungstypen 4 und 5, wie anhand der Reaktionsprodukte 4d und 5d gezeigt werden konnte. Während Trimethyl- und Triethylphosphit (2a bzw. 2b) mit den 2-Chlorvinylketonen 1 a - 1d jeweils die Produktgemische 3a-3e, 4a-4e und 5a-5e liefern, entstehen bei Verwendung von Triisopropylphosphit (2c) bisweilen nur Reaktionsprodukte des im Titel genannten Typs 3. So liefert 2c mit 1a nur ein Gemisch aus der Hauptmenge des 2-Acylvinylphosphonats 3f und des in untergeordneter Menge auftretenden 3-Oxo-1,1-alkandiyidiphosphonats 5f. Nach Umsetzung von 2c mit 1d wird als definiertes Reaktionsprodukt nur noch das 2-Acylvinylphosphonat 3g isoliert.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.197919790410
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  • 10
    Electronic Resource
    Electronic Resource
    Biosynthese von Naturstoffen mit einer P—C-Bindung, I. Einbau von D-[6,6-D2]Glucose in (2-Aminoethyl)phosphonsäure in Tetrahymena thermophila (1988)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1988 (1988), S. 531-535 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Biosynthesis of Natural Products with a P—C Bond, I. - Incorporation of D-[6,6-D2]Glucose into (2-Aminoethyl)phosphonic Acid in Tetrahymena thermophilaThe phosphate-phosphonate rearrangement is tested as a model reaction for the biosynthesis of the P—C bond as alternative to the rearrangement of phosphoenolpyruvate. D-[6,6-D2]glucose was prepared and added to the growth medium of Tetrahymena thermophila. (2-Aminoethyl)phosphonic acid (AEP) (1) was isolated from the wet cell mass by hydrolysis with 6 N HCl and ion exchange chromatography and was derivatized to the crystalline 4-bromobenzamide 26. The amount of [1,1-D2]-AEP in admixture with unlabeled AEP was up to 43%, which is not in agreement with an enzymic phosphate-phosphonate rearrangement of dihydroxyacetone phosphate, for which monodeutereated AEP would be expected. For comparison [1,1-D2]-AEP (31) was prepared starting from 2-amino-[1,1-D2]ethanol.
    Notes: Es wird untersucht, ob die Phosphat-Phosphonat-Umlagerung als Modellreaktion für die Biosynthese der P—C-Bindung als Alternative zur Umlagerung der Phosphoenolbrenztraubensäure dienen kann. D-[6,6-D2]Glucose wurde hergestellt und dem Nährmedium von Tetrahymena thermophila zugefügt. Aus der feuchten Zellmasse wurde durch Hydrolyse mit 6 N HCl und Ionenaustauscherchromatographie (2-Aminoethyl)phosphonsäure (AEP) (1) gewonnen und in das kristalline 4-Brombenzamid 26 übergeführt. Der Gehalt an [1,1-D2]-AEP beträgt bis zu 43% neben im wesentlichen nichtmarkierter AEP, was mit einer enzymatischen Phosphat-Phosphonat-Umlagerung von Dihydroxyacacetonphosphat nicht vereinbar ist, für die monodeuterierte AEP zu erwarten wäre. Für Vergleichszwecke wurde ausgehend vom 2-Amino-[1,1-D2]ethanol durch Umfunktionalisierung [1,1-D2]-AEP (31) gewonnen.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198819880607
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