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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

✍ Scribed by Hiroki Kumamoto; Satoru Shindoh; Hiromichi Tanaka; Eisen Gen; Kazuhiro Haraguchi; Atsushi Kittaka; Tadashi Miyasaka

Book ID
104259209
Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
215 KB
Volume
39
Category
Article
ISSN
0040-4039

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✦ Synopsis

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 variously substituted at the 2'-position. Desilylation of these compounds caused no further elimination, and furnished a hitherto unknown series of nucleoside analogues.

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