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
URL:
http://dx.doi.org/10.1002/jlac.1990199001110
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