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A new route to 2′,3′-dideoxycytidine

✍ Scribed by Motawia, Mohammed S. ;Pedersen, Erik B.

Publisher
John Wiley and Sons
Year
1990
Tongue
English
Weight
384 KB
Volume
1990
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

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 N^4^‐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.

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