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- W2167003694 abstract "The regiospecific reaction of 5-vinyl-3′,5′-di-O-acetyl-2′-deoxyuridine (2) with HOX (X = Cl, Br, I) yielded the corresponding 5-(1-hydroxy-2-haloethyl)-3′,5′-di-O-acetyl-2′-deoxyuridines 3a-c. Alternatively, reaction of 2 with iodine monochloride in aqueous acetonitrile also afforded 5-(1-hydroxy-2-iodoethyl)-3′,5′-di-O-acetyl-2′-deoxyuridine (3c). Treatment of 5-(1-hydroxy-2-chloroethyl)- (3a) and 5-(1-hydroxy-2-bromoethyl)-3′,5′-di-O-acetyl-2′-deoxyuridine (3b) with DAST (Et2NSF3) in methylene chloride at -40° gave the respective 5-(1-fluoro-2-chloroethyl)- (6a, 74%) and 5-(1-fluoro-2-bromoethyl)-3′,5′-di-O-acetyl-2′-deoxyuridine (6b, 65%). In contrast, 5-(1-fluoro-2-iodoethyl)-3′,5′-di-O-acetyl-2′-deoxyuridine (6e) could not be isolated due to its facile reaction with methanol, ethanol or water to yield the corresponding 5-(1-methoxy-2-iodoethyl)- (6c), 5-(1-ethoxy-2-iodoethyl)- (6d) and 5-(1-hydroxy-2-iodoethyl)-3′,5′-di-O-acetyl-2′-deoxyuridine (3c). Treatment of 5-(1-hydroxy-2-chloroethyl)- (3a) and 5-(1-hydroxy-2-bromoethyl)-3′,5′-di-O-acetyl-2′-deoxyuridine (3b) with thionyl chloride yielded the respective 5-(1,2-dichloroethyl)- (6f, 85%) and 5-(1-chloro-2-bromoethyl)-3′,5′-di-O-acetyl-2′-deoxyuridine (6g, 50%), whereas a similar reaction employing the 5-(1-hydroxy-2-iodoethyl)- compound 3c afforded 5-(1-methoxy-2-iodoethyl)-3′,5′-di-O-acetyl-2′-deoxyuridine (6c), possibly via the unstable 5-(1-chloro-2-iodoethyl)-3′,5′-di-O-acetyl-2′-deoxyuridine intermediate 6h. The 5-(1-bromo-2-chloroethyl)- (6i) and 5-(1,2-dibromoethyl)-3′,5′-di-O-acetyl-2′-deoxyuridine (6j) could not be isolated due to their facile conversion to the corresponding 5-(1-ethoxy-2-chloroethyl)- (6k) and 5-(1-ethoxy-2-bromoethyl)-3′,5′-di-O-acetyl-2′-deoxyuridine (61). Reaction of 5-(1-hydroxy-2-bromoethyl)-3′,5′-di-O-acetyl-2′-deoxyuridine (3b) with methanolic ammonia, to remove the 3′,5′-di-O-acetyl groups, gave 2,3-dihydro-3-hydroxy-5-(2′-deoxy-β-D-ribofuranosyl)-furano[2,3-d]pyrimidine-6(5H)-one (8). In contrast, a similar reaction of 5-(1-fluoro-2-chloroethyl)-3′,5′-di-O-acetyl-2′-deoxyuridine (6a) yielded (E)-5-(2-chlorovinyl)-2′-deoxyuridine (1b, 23%) and 5-(2′-deoxy-β-D-ribofuranosyl)furano[2,3-d]pyrimidin-6(5H)-one (9, 13%). The mechanisms of the substitution and elimination reactions observed for these 5-(1,2-dihaloethyl)-3′,5′-di-O-acetyl-2′-deoxyuridines are described." @default.
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- W2167003694 date "2010-08-22" @default.
- W2167003694 modified "2023-09-26" @default.
- W2167003694 title "ChemInform Abstract: Synthesis and Properties of 5-(1,2-Dihaloethyl)-2′-deoxyuridines and Related Analogues." @default.
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- W2167003694 doi "https://doi.org/10.1002/chin.199220287" @default.
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