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An Intramolecular Anionic Migration of a Stannyl Group from the 6-Position of 1-(2-Deoxy-d-erythro-pent-1-enofuranosyl)uracil to the 2′-Position: Synthesis of 2′-Substituted 1′,2′-Unsaturated Uridines

✍ Scribed by Hiroki Kumamoto; Satoru Shindoh; Hiromichi Tanaka; Yoshiharu Itoh; Kazuhiro Haraguchi; Eisen Gen; Atsushi Kittaka; Tadashi Miyasaka; Masato Kondo; Kazuo T Nakamura

Book ID
108370870
Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
173 KB
Volume
56
Category
Article
ISSN
0040-4020

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We report that TBDMS-protected l-(2-deoxy-D-erythro-pent-l-enofuranosyl)-6-(tributylstannyl)uracil, when treated with LDA or LTMP, undergoes an anionic stannyl migration to yield the 2'-stannylated product. Optimization of the reaction conditions has disclosed an efficient entry to compounds various

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Stannyl Migration from the Base to the Sugar Portion of 1',2'-Unsaturated Uridine: The First Example of Substitution at the 2'-Position. -Treatment of the stannylated uracil (III) with base under optimized conditions results in anionic stannyl migration to give the 2'-stannylated product (V). It ca