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  • 1-[1,7-Dicarba-closo-dodecaboran(12)-1-yl]aldoses  (1)
  • 4-O-Alkyl-D-glucoses  (1)
  • 1
    Electronic Resource
    Electronic Resource
    Amphiphilic Carbohydrate-based Mesogens, IX. Mesogenic 4-O-Alkyl-D-glucoses via Methyl 4,6-O-Alkylidene-D-glucopyranosides (1993)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1993 (1993), S. 1063-1067 
    Details
    ISSN: 0170-2041
    Keywords: Carbohydrates ; 4-O-Alkyl-D-glucoses ; Liquid crystals, smectic ; Bromodiethylborane-sodium triethylhydroborate reducing system ; Amphiphilic glucoses ; X-ray diffraction, small angle ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The 4,6-O-alkylidene derivatives (hexylidene-decylidene, 2a-e) are prepared by condensation of methyl α- or β-D-glucopyranoside 1 with alkanals in the presence of pyridinium tosylate. O-diethylborylation of 2 gives 3 which are allowed to react firstly with bromodiethylborane and subsequently with sodium triethylhydroborate to yield methyl 4-O-alkyl-D-glucopyranosides 5 after deborylation. Acid hydrolysis of 5 gives mesogenic 4-O-alkyl-D-glucopyranoses 6a-e. The amphiphilic 6 exhibit the smectic A liquid crystalline phase on melting.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1993199301171
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  • 2
    Electronic Resource
    Electronic Resource
    1-[1,7-dicarba-closo-dodecaboran(12)-1-yl]aldoses: Novel Boron Neutron Capture Candidates (1993)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1993 (1993), S. 831-835 
    Details
    ISSN: 0170-2041
    Keywords: Boron neutron capture therapy ; 1-[1,7-Dicarba-closo-dodecaboran(12)-1-yl]aldoses ; 1-[m-Carboran-1-yl]aldoses ; Boranes ; Carbohydrates ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Monolithiated 1,7-dicarba-closo-dodecaborane(12) reacts with O-isopropylidene derivatives of D-erythrono-1,4-lactone (1), L-mannono-1,4-lactone (3) and with tetra-O-trimethylsilylated D-glucono-1,5-lactone (2) and D-gulono-1,4-lactone (4) to give the title compounds after deprotection. An X-ray structure analysis of the protected L-mannofuranose carborane derivative 9 reveals that the more stable anomer has the β-L configuration.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1993199301131
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