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  • 1
    Electronic Resource
    Electronic Resource
    Eine neuartige Eliminierungsreaktion an Kohlenhydraten Synthese des Methyl-4,6-O-benzyliden-3-desoxy-2-O-methyl-α-D-erythro-hex-2-enopyranosids (1975)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 108 (1975), S. 1896-1901 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: A New Elimination Reaction in Carbohydrates. Synthesis of Methyl 4,6-o-benzylidene-3-deoxy-2-o-methyl-α-D-erythro-hex-2-enopyranosideThe methyl 4,6-O-benzylidene-2,3-di-O-methylhexopyranosides with D-gluco- (1), D-altro- (3) and D-allo-configuration (4) react with n-butyllithium by methanol elimination to give methyl 4,6-O-benzylidene-3-deoxy-2-O-methyl-α-D-erythro-hex-2-enopyranoside (2) in a yield of 30% (from 1), 45% (from 3), or 55% (from 4).
    Notes: Die Methyl-4,6-O-benzyliden-2,3-di-O-methylhexopyranoside mit D-gluco- (1), D-altro- (3) und D-allo-Konfiguration (4) reagieren mit n-Butyllithium unter Methanol-Eliminierung zu Methyl-4,6-O-benzyliden-3-desoxy-2-O-methyl-α-D-erythro-hex-2-enopyranosid (2) in Ausbeuten von 30% (aus 1), 45% (aus 3) oder 55% (aus 4).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19751080612
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  • 2
    Electronic Resource
    Electronic Resource
    Reaktionen von Acetalen der L-Rhamnose mit Lithiumorganylen Neue Synthesen von Mycaral, Olivomycal und Methyl-2,3,6-tridesoxy-α-L-erythro-hex-2-enopyranosid (1981)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 114 (1981), S. 740-745 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Reactions of Acetals of L-Rhamnose with Lithium-organic Compounds New Syntheses of Mycaral, Olivomycal, and Methyl 2,3,6-Trideoxy-α-L-erythro-hex-2-enopyranosideMethyl α-L-mycaroside (6a) is obtained from the dideoxy-uloside 2) by Grignard addition. the benzylidene rhamnoside (1a) reacts with methyllithium to give in only one step mycaral (4) (21%) and olivomycal (5) (72%). With lithiumdiisopropylamide 1a yields the unsaturated sugar 3a.
    Notes: Methyl-α-L-mycarosid (6a) wird aus dem Didesoxy-ulosid 2 durch Grignard-Addition erhalten. Das Benzylidenrhamnosid 1a reagiert mit Methyllithium in einem schritt zu Mycaral (4) und Olivomycal (5). Mit Lithiumdiisopropylamid erhält man hingegen aus 1a den ungesättigten Zucker 3a.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19811140233
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  • 3
    Electronic Resource
    Electronic Resource
    Reaktionen von O-Isopropyliden- und O-Hexylidenzuckern mit n-Butyllithium zu neuen ungesättigten Kohlenhydraten (1978)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 111 (1978), S. 1514-1520 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Reactions of O-Isopropylidene and O-Hexylidene Sugars with n-Butyllithium Forming Novel Unsaturated CarbohydratesThe 1,2-O-isopropylidene and -hexylidene-3-O-methyl D-derivatives of fructose 3b,c react with n-butyllithium to give the corresponding isomeric 1,2-enediol derivatives 4b,c The 2-deoxy-3,4-O-isopropylideneriboside 5 yields the glycal derivative 7 and the 4,5-unsaturated 2-deoxyriboside 6. The psicose derivative. 8. the C-3-epimer of 3a, reacts by acetone elimination to give the 3.4-unsaturated ulose 9. Steric and electronic effects control the different reaction pathways.
    Notes: Die 1,2-O-Isopropyliden- bzw. -Hexyliden-3-O-methyl-D-Derivate der Fructose 3b,c reagieren mit n-Butyllithium zu den isomeren entsprechenden 1,2-Endiol-Derivaten 4b,c Das 2-Desoxy-3,4-O-isopropyhdenribosid 5 liefert das Glycal-Derivat 7 und das 4,5-ungesättigte 2-Desoxy-ribosid 6. Das zu 3a C-3-epimere Psicose-Derivat 8 reagiert unter Aceton-Eliminierung zu der 3,4-ungesättigten Ulose 9. Sterische und elektronische Effekte steuern die verschiedenen Reaktionswege.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19781110431
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  • 4
    Electronic Resource
    Electronic Resource
    Synthese von 1-N-Acetyl-2-chlor-2-desoxyhexose-Derivaten (1979)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 112 (1979), S. 3063-3071 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis of 1-N-Acetyl-2-chloro-2-deoxyhexose DerivativesAnodic addition of chloride ions to the activated double bond of the unsaturated sugars 1, 4, and 6 in the presence of acetonitrile leads to the following hitherto unknown compounds: 1-N-acetyl-3,4,6-tri-O-acetyl-2chloro-2-deoxy-β-D-glucopyranosylamine (2), 1-N-acetyl-3,4,6-tri-Oacetyl-2-deoxy-β-D-mannopyranosylamine (3), 1-N-acetyl-3,4,6-tri-O-acetyl-2-chloro-2 deoxy-α-D-galactopyranosylamine (5) and 5-chloro-5-deoxy-2,3-O-isopropylidene-1-O-methyl-β-D-threo-hexulo-5-enopyranose (7).
    Notes: Durch anodische Addition von Chlorid-Ionen an die aktivierte Doppelbindung der ungesättigten Zucker 1, 4 und 6 in Gegenwart von Acetonitril werden folgende Verbindungen synthetisiert: 1-N-Acetyl-3,4,6-tri-O-acetyl-2-chlor-2-desoxy-β-D-glucopyranosylamin (2), 1-N-Acetyl-3,4,6-tri-O-acetyl-2-chlor-2-desoxy-β-D-mannopyranosylamin (3), 1-N-Acetyl-3-4-6-tri-O-acetyl-2-chlor-2-desoxy-α-D-galactopyranosylamin (5) und 5-Chlor-5-desoxy-2,3-O-isopropyliden-1-O-1-O-methyl-β-D threo-hexulo-5-enopyranose(7).
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19791120904
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  • 5
    Electronic Resource
    Electronic Resource
    Reaktionen von Acetalen der L-Sorbose mit n-Butyllithium (1980)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 113 (1980), S. 1761-1767 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Reactions of Acetals of L-Sorbose with n-Butyllithium2,3:4,6-Di-O-isopropylidene-α-L-sorbose (1a) gives with n-butyllithium the known 6-deoxy-2,3-O-isopropylidene-β-D-threo-hex-5-enulofuranose (2), while the corresponding benzylidene compound 4 yields the glycal derivative 2,5-anhydro-4,6-O-benzylidene-3-deoxy-L-threo-hex-2-enitol (5). The 1-benzyl ether 1b is converted into 3 by Wittig rearrangement. Under analogous conditions both possible Wittig rearrangement products 7a and b are obtained from methyl 6-O-benzyl-2,3,4-tri-O-methyl-α-D-glucopyranoside (6). Their configuration is established by 1H NMR spectroscopy.
    Notes: 2,3:4,6-Di-O-isopropyliden-α-L-sorbose (1a) ergibt mit n-Butyllithium die bekannte 6-Desoxy-2,3-O-isopropyliden-β-D-threo-hex-5-enulofuranose (2), während die entsprechende Benzylidenverbindung 4 das Glycal-Derivat 2,5-Anhydro-4,6-O-benzyliden-3-desoxy-L-threo-hex-2-enitol (5) liefert. Aus dem 1-Benzylether 1b entsteht u. a. durch Wittig-Umlagerung das Produkt 3. Unter den gleichen Bedingungen werden aus Methyl-6-O-benzyl-2,3,4-tri-O-methyl-α-D-glucopyranosid (6) beide möglichen Wittig-Umlagerungsprodukte 7a und 7b erhalten. Ihre Konfigurationszuordnung erfolgt aus dem 1H-NMR-Spektrum.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19801130511
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  • 6
    Electronic Resource
    Electronic Resource
    Eine einfache Synthese von Methyl-4,6-O-benzyliden-2-desoxy-α-D-erythro-hexopyranosid-3-ulose (1974)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 107 (1974), S. 2612-2614 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: A Simple synthesis of Methyl 4,6-O-Benzylidene-2-desoxy-α-D-erythro-hexopyranosid-3-uloseMethyl 2,3:4,6-di-O-benzylidene-α-D -mannopyranoside (1) reacts with 2 mol n-butyllithium under cycloelimination to give methyl 4,6-O-benzylidene-α-D-erythro-hexopyranosid-3-ulose (2) (70%) and 1-phenyl-1-pentanol (3).
    Notes: Methyl-2,3:4,6-di-O-benzyliden-α-D-mannopyranosid (1) reagiert mit 2 Moläquivv, n-Butyl-lithium unter Cycloeliminierung zu Methyl-4,6-O-benzyliden-α-D-erythro-hexopyranosid-3-ulose (2) (ca. 70%) und 1-Phenyl-1-pentanol (3).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19741070821
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  • 7
    Electronic Resource
    Electronic Resource
    Umsetzungen von 1,2-O-Isopropylidenzuckern mit n-Butyllithium zu acyclischen Olefinen (1976)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 109 (1976), S. 1708-1723 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Reactions of 1,2-O-Isopropylidene Sugars with n-Butyllithium to Acyclic olefinsThe reaction of four different 1,2-O-isopropylidene sugar derivates 3-6 with n-butyllithium yields the hitherto unknown acyclic olefins 7a-12a the structures of which are characterized by spectroscopic and chemical methods. The different reaction-pathways are discussed.
    Notes: Die Reaktion von 4 verschiedenen 1,2-O-Isopropylidenzucker-Derivaten 3-6 mit n-Butyllithium führt zu bisher unbekannten, acyclischen Olefinen 7a-12a, deren Konstitution an Hand spektroskopischer und chemischer Methoden aufgeklärt wird. Die verschiedenen Reaktionswege werden diskutiert.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19761090515
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  • 8
    Electronic Resource
    Electronic Resource
    Reaktionen von O-Isopropylidenzuckern mit lithiumorganischen Verbindungen zu ungesättigten Zuckern Synthese von 4-Desoxy-4-eno-β-D-threo-pentose- und 5-Desoxy-5-eno-β-D-threo-hexulose-Derivaten (1976)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 109 (1976), S. 2849-2861 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Reaction of O-Isopropylidene Sugars with Lithium-organic Compounds Forming Unsaturated Sugars Synthesis of 4-Deoxy-4-eno-β-eno-D-threo-pentose- and 5-Deoxy-5-eno-β-D-threo-hexulose DerivativesThe 3,4- and 4,5-O-isopropylidene derivatives ofD-arabinose D-fructose1. 9 and 4, 5 react with lithium-organic compounds by acetone elimination to give the unsaturated sugars 3, 10 and 6,7. In addition the 1-benzyl ether 5 yields 8 via Wittig-rearrangement and chain-prolongation.  -  Constitution and conformation of the new compounds are elucidated by spectroscopic methods.
    Notes: Die 3,4-bzw. 4,5-O-Isopropyliden-Derivate der-D-Arabinose und D-Fructose 1, 9 und 4, 5 Reagieren mit lithiumorganischen Verbindungen unter Aceton-Eliminierung zu den ungesättigten Zuckern 3, 10, und 6, 7. Aus dem 1-Benzyläther 5 entsteht außerdem durch Wittig-Umlagerung und Kettenverlängerung 8. - Konstitution und Konformation der neuen Verbindungen werden mittels spektroskopischer methoden aufgeklärt.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19761090817
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  • 9
    Electronic Resource
    Electronic Resource
    Reaktionen von Kohlenhydrat-acetalen mit Organolithiumverbindungen Eine einfache Synthese der 4,6-Didesoxy-α-D-erythro-hexopyranos-3-ulose (1981)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 114 (1981), S. 1192-1195 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Reactions of Acetals of Sugars with Organolithium Compounds A Simple Synthesis of 4,6-Dideoxy-α-D-erythro-hexopyranos-3-ulose1,2:3,4-Di-O-isopropylidene-β-L-arabinose (3) reacts with lithium diisopropylamide to give the 4-deoxy-4-eno sugar 4. After its oxidation a stereospecific 1,4-addition by methyllithium/copper (I) iodide yields the 4,6-dideoxy-3-ulose 6.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19811140338
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  • 10
    Electronic Resource
    Electronic Resource
    Synthese und Hydrolyse von Amadori-Verbindungen aus 2-Amino-2-desoxy-D-hexosen und D-Hexuronsäuren (1979)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1979 (1979), S. 1682-1688 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis and Hydrolysis of Amadori Rearrangement Products from 2-Amino-2-deoxy-D-hexoses and D-Hexuronic AcidsCondensation of 2-amino-2-deoxyhexoses (D-gluco or D-galacto configuration) with hexuronic acids (D-gluco or D-galacto configuration) in methanol gave the Amadori rearrangement products 6-(2-deoxy-α-D-glucopyranos-2-ylamino)-6-deoxy-β-D- lyxo-5-hexulofuranosonic acid (1) and -α-D-arabino-5-hexulofuranosonic acid (2) as well as 6-(2-deoxy-D-galactopyranos-2-ylamino)-6-deoxy-β-D lyxo-5-hexulofuranosonic acid · H2O (3), and -α-D-arabino-5-hexulofuranosonic acid · H2O (4). The compounds 1-4 were characterized by analytical and 13C-NMR spectroscopic data. At pH 6.5 they split quantitatively into the original compounds.
    Notes: In Methanol erhält man aus D-gluco- bzw. D-galacto-konfigurierten 2-Amino-2-desoxyhexosen sowie Hexuronsäuren die Amadori-Verbindungen 6-(2-Desoxy-α-D-glucopyranos-2-ylamino)-6-desoxy-β -D-lyxo-5-hexulofuranosonsäure (1) und -α-D-arabino-5-hexulofuranosonsäure (2) sowie 6-(2-Desoxy-D-galactopyranos-2-ylamino)-6-desoxy-β-D- lyxo-5-hexulofuranosonsäure · H2O (3) und -α-D-arabino-5-hexulofuranosonsäure · H2O (4). Die Verbindungen 1-4 werden durch elementaranalytische und 13C-NMR-spektroskopische Daten charakterisiert. Bei pH 6.5 zerfallen sie fast quantitativ unter Rückbildung der eingesetzten Ausgangsverbindungen.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.197919791107
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