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  • 1970-1974  (5)
  • 1971  (5)
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  • 1970-1974  (5)
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  • 1
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 104 (1971), S. 830-836 
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Preparation of 1.6-Anhydro-β-D-mannofuranose and 1.6-Anhydro-α-L-gulofuranoseVacuum pyrolysis of D-mannose yields 1.6-anhydro-β-D-mannopyranose besides 1.6-anhydro-β-D-mannofuranose (1a), which can be obtained in an overall yield of 3.3% by direct crystallisation. RuO4-Oxidation of the 2.3-O-isopropylidene derivative of 1 a leads to the formation of 1.6-anhydro-2.3-O-isopropylidene-β-D-lyxo-hexofuranos-5-ulose (3), which is reduced with LiAlH4 stereoselectively to the corresponding 1.6-anhydro-α-L-gulofuranose derivative 4.
    Notes: Durch Vakuumpyrolyse von D-Mannose ist neben 1.6-Anhydro-β-D-mannopyranose die 1.6-Anhydro-β-D-mannofuranose (1 a) direkt in 3.3 proz. Ausb. kristallisiert gewinnbar. RuO4-Oxydation der 2.3-Isopropyliden-Verbindung von 1 a ergibt 1.6-Anhydro-2.3-O-isopropyliden-β-D-lyxo-hexofuranos-5-ulose (3), die mit LiAlH4 selektiv zum 1.6-Anhydro-α-L-gulofuranose-Derivat 4 hydriert wird.
    Type of Medium: Electronic Resource
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  • 2
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 104 (1971), S. 3096-3100 
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Preparation of Enediol Acetates from 1.6-anhydro-β-D-hexopyranosulosesTreatment of the 1.6-anhydro-β-D-hexopyranos-3-uloses 1 and 3 with acetic anhydride in pyridine leads in good yield to the erythro-enediol acetates 2 and 6 by regioselective participation of the vicinal axial protons. None of the threo-acetates 4 and 5 was detected. 4 and 5 can also not be prepared from the unprotected uloses 7 and 9, but by acetylating the protected keto-sugar 10 the isopropylidene derivative 11 with threo-configuration is obtained.
    Notes: Die Behandlung der 1.6-Anhydro-β-D-hexopyranos-3-ulosen 1 und 3 mit Acetanhydrid in Pyridin liefert in guter Ausbeute die erythro-Endiolacetate 2 und 6 unter regioselektiver Beteiligung der vicinalen axialen Wasserstoffatome. Die threo-Acetate 4 und 5 werden nicht beobachtet. Sie können auch nicht aus den freien 4- bzw. 2-Ulosen 7 und 9 gewonnen werden. Durch Acylierung der geschützten Ketose 10 ist es jedoch möglich, das Isopropylidenderivat 11 mit threo-Konfiguration darzustellen.
    Type of Medium: Electronic Resource
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  • 3
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 104 (1971), S. 3835-3841 
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Dimeric Hemiacetals of 1.6-Anhydrohexosulose, II. Preparation and Structure Determination of Dimeric Hemiacetals of 1.6-Anhydro-β-D-lyxo-hexopyranosulosesThe 1.6-anhydro-β-D-lyxo-hexopyranosuloses 1 and 3 with to the carbonyl group vicinal axial hydroxyl groups can be isolated under appropriate conditions as dimeric hemiacetals 4a and 5a, resp. The dimer 4a is symmetrically 3.4-cis linked, thus establishing a central 1.4-dioxane ring. On the other hand in 5a two monomers are connected unsymmetrically by an 1.3-dioxolane ring. The linkage is 2′.3′-cis to C-2. The lyxo-ulose 2 with two vicinal equatorial hydroxyl groups adjacent to CO yields no dimeric hemiacetals.
    Notes: Die 1.6-Anhydro-β-D-lyxo-hexopyranosulosen 1 und 3 mit zur Carbonylgruppe benachbarten axialen Hydroxylgruppen können unter geeigneten Bedingungen als dimere Halbacetale 4a bzw. 5a isoliert werden. Das Dimere 4a ist unter Bildung eines zentralen 1.4-Dioxanringes symmetrisch 3.4-cis-verknüpft. Demgegenüber sind in Verbindung 5a zwei Monomere unsymmetrisch über einen 1.3-Dioxolanring verbunden. Die Verknüpfung erfolgt 2′.3′-cis nach C-2. Die lyxo-Ulose 2 mit zwei zur Carbonylgruppe benachbarten äquatorialen Hydroxylgruppen bildet keine dimeren Halbacetale.
    Type of Medium: Electronic Resource
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  • 4
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 104 (1971), S. 2063-2070 
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Selective Catalytic Oxidations, XXVIII. Catalytic Oxidation of 1.6-Anhydro-α-D-galactofuranose. Preparation of 1.6-Anhydro-β-L-altrofuranose1,6-Anhydro-β-D-glucofuranose (1) and 1,6-anhydro-α-D-galactofuranose (3) were subjected to conditions of catalytic oxidation. Only compound 3 was oxidized at the equatorial 5-hydroxyl group to 1,6-anhydro-β-L-arabino-hexofuranos-5-ulose (4). The ketosugar 4 was reduced stereoselectively with Pd-C/H2 to 1,6-anhydro-β-L-altrofuranose (2). 1.6% of compound 2 was detected in acidic medium in the equilibrium of altrose. The optical rotation of 2 is in good agreement with a calculated value.
    Notes: 1.6-Anhydro-β-D-glucofuranose (1) und 1.6-Anhydro-α-D-galaktofuranose (3) wurden den Bedingungen der katalytischen Oxydation unterworfen, wobei nur 3 an der äquatorialen 5-Hydroxylgruppe zur 1.6-Anhydro-β-L-arabino-hexofuranos-5-ulose (4) oxydiert wurde. Die Ketose 4 konnte stereoselektiv mit Pd-C/H2 zur 1.6-Anhydro-β-L-altrofuranose (2) reduziert werden. Die Anhydroverbindung 2 wurde zu 1.6% im sauren Medium im Gleichgewicht der Altrose nachgewiesen. Die optische Drehung von 2 steht in Übereinstimmung mit einem berechneten Wert.
    Type of Medium: Electronic Resource
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  • 5
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 104 (1971), S. 2553-2566 
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Preparation, Structure Determination and Reactions of the Dimeric 1.6-Anhydro-β-D-hexopyranos-3-uloses1.6-Anhydro-β-D-xylo-hexopyranos-3-ulose (2) crystallizes as a symmetrical 2.3-cis-linked dimeric hemiacetal 5a, in which each axial 2-hydroxy group is connected with the corresponding 3-keto group of a second molecule. Crystalline 1.6-anhydro-β-D-arabino-hexopyranos-3-ulose (3) proved to be a dimer 6a with a symmetrical 3.4-cis linkage between the 4-hydroxy group and the 3-keto group of the other molecule. 1.6-Anhydro-β-D-ribo-hexopyranos-3-ulose (1) with axial hydroxy groups at C-2 and C-4 crystallizes as 1:1 mixture of two dimers 15, and 16, one of which is 2.3-cis, the other 3.4-cis linked.
    Notes: 1.6-Anhydro-β-D-xylo-hexopyranos-3-ulose (2) kristallisiert als symmetrisch 2.3-cis-verknüpftes dimeres Halbacetal 5a, in dem die axiale Hydroxylgruppe an C-2 jeweils mit der 3-Ketogruppe eines zweiten Moleküls verbunden ist. Kristallisierte 1.6-Anhydro-β-D-arabino-hexopyranos-3-ulose (3) stellt ein Dimeres 6a mit symmetrischer 3.4-cis-Verknüpfung der axialen Hydroxylgruppe am C-4 mit der 3-Ketogruppe des anderen Moleküls dar. 1.6-Anhydro-β-D-ribo-hexopyranos-3-ulose (1) mit axialer Hydroxylgruppe an C-2 und C-4 kristallisiert als 1:1-Gemisch von zwei Dimeren 15 und 16, von denen das eine 2.3-cis-, das andere 3.4-cis-verknüpft ist.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
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