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- W2953158116 abstract "The reaction of 3-N-3′,5′-di-O-tribenzoyl-2′-deoxy-5-vinyluridine (2) with dibromocarbene, generated from PhHgCBr3 under thermal neutral conditions, yielded a mixture of the 5-[(1S)-2,2-dibromocyclopropyl]- (3a) and 5-[(1R)-2,2-dibromocyclopropyl]-3-N-3′,5′-di-O-tribenzoyl-2′-deoxy-5-vinyluridine (4a) diastereomers, which were separated (1:1 ratio). Treatment of 3a and 4a with methanolic ammonia afforded the respective 5-[(1S)-2,2-dibromocyclopropyl]- (3b) and 5-[(1R)-2,2-dibromocyclopropyl]-2′-deoxyuridines (4b). The absolute configuration of 3b has been established by X-ray crystal structure determination. Monodebromination of 3b, using zinc dust in HOAc at 50 °C, gave a mixture of the 5-[(1S,2S)-2-bromocyclopropyl]- (5) and 5-[(1S,2R)-2-bromocyclopropyl]- (6) diastereomers, which were separated and their respective configuration assigned by 1H nuclear magnetic resonance. A similar monodebromination of 4b yielded the 5-[(1R,2R)-2-bromocyclopropyl]- (7) and 5-[(1R,2S)-2-bromocyclopropyl]-2′-deoxyuridine ..." @default.
- W2953158116 created "2019-06-27" @default.
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- W2953158116 date "1990-02-06" @default.
- W2953158116 modified "2023-09-26" @default.
- W2953158116 title "ChemInform Abstract: Synthesis, Separation, and Absolute Configuration of the Two 5-(2,2-Dibromocyclopropyl) and Four 5-(2-Bromocyclopropyl) Diastereomers of 2′-Deoxyuridine." @default.
- W2953158116 cites W2090491463 @default.
- W2953158116 doi "https://doi.org/10.1002/chin.199006308" @default.
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