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  • 1
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1991 (1991), S. 879-883 
    ISSN: 0170-2041
    Keywords: Nucleosides, convergent synthesis ; Nucleosides, 2′,3′-dideoxy- ; Nucleosides, 2′,3′-didehydro- ; Adenine, N6N6-dimethylnucleosides ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The trimethylsilyated 6-dimethylaminopurine 1 was coupled with the 2′,3′-dideoxyribose derivatives 2a, b and 7 by using trimethylsilyl triflate as catalyst to yield the corresponding nucleosides 3a, b, 4a, b and 8, which were appropriately deprotected to give the desired nucleosides 5a, b and 9 as well as the related α-isomers 6a, b and 10. The 2-deoxyribose derivative 12 was mesylated at the 3′-O-position to give 13 which was coupled similarly with 1 to yield compound 14 and its α-anomer 15. Compounds 14 and 15 were treated with tetrabutylammonium fluoride to give the desired 2′,3′-didehydro-2′,3′-dideoxynucleoside analogue 16 and its α-anomer 17.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
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  • 2
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1990 (1990), S. 599-602 
    ISSN: 0170-2041
    Keywords: Glycosidation ; 4-Biphenylcarbonyl protecting group ; Barton deoxygenation ; 2′,3′-Dideoxycytidine ; Nucleosides, 2′,3′-dideoxy- ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 2-Deoxy-D-ribose (1) was converted into its methyl glycofuranoside 2, which was treated with 4-biphenylcarbonyl chloride to give a separable mixture of 3 (26%) and 4 (40%). Compounds 3 and 4 were deoxygenated by Barton deoxygenation to give the corresponding 2,3-dideoxyribose derivatives 7 and 8 in good yields as crystalline materials. Reaction of 7 and 8 with the silylated N4-isobutyrylcytosine 9, using trimethylsilyl triflate as catalyst afforded a separable mixture of the protected 2′,3′-dideoxynucleosides 10 (29%) and 11 (31%) which were deprotected with methanolic ammonia to give 2′,3′-dideoxycytidine (12) and its α-anomer 13.
    Type of Medium: Electronic Resource
    Library Location Call Number Volume/Issue/Year Availability
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