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- W2068313458 abstract "A method was developed to prepare 5′-deoxy-5′-substituted-ψ-uridine derivatives 4 from 3′,5′-O-(1, 1, 3, 3-tetraisopropyldisiloxanyl)-1,3-dimethyl-ψ-uridine 1 via a silyl rearrangement reaction. Nucleophilic displacement of the mesyloxy function of 2′-O-mesyl-1,3-dimethyl-ψ-uridine 7 afforded products with the 2′-substituent in the “down” ribo configuration 8. X-Ray crystallographic analysis of the 2′-chloro derivative 8a firmly established the molecular structure of 8 and provided evidence for neighboring group participation of the 4-carbonyl function of 7 during the nucleophilic reactions. Treatment of 1,3-dimethyl-ψ-uridine 11 with α-acetoxyisobutyryl chloride afforded a mixture from which two 2′-chloro-2′-deoxy-C-nucleosides were obtained. The major product (33% yield) was identical with 8. The minor product (7% yield) was consequently assigned the arabino nucleoside 14. This is the first direct introduction of a 2′-substituent in the “up” configuration in a preformed pyrimidine nucleoside." @default.
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- W2068313458 date "1985-11-01" @default.
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- W2068313458 title "Nucleosides.<b>130</b>. Synthesis of 2′-Deoxy-2′-substituted- and 5′-Deoxy-5′-substituted-ψ-uridine Derivatives. Crystalline and Molecular Structure of 2′-Chloro-2′-deoxy-1,3-dimethyl-ψ-uridine. Studies Directed Toward the Synthesis of 2′-Deoxy-2′-substituted-<i>arabino</i>-Nucleosides.<b>1</b>" @default.
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- W2068313458 doi "https://doi.org/10.1002/jhet.5570220646" @default.
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