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ChemInform Abstract: 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 H. KUMAMOTO; S. SHINDOH; H. TANAKA; E. GEN; K. HARAGUCHI; A. KITTAKA; T. MIYASAKA

Publisher
John Wiley and Sons
Year
2010
Weight
40 KB
Volume
29
Category
Article
ISSN
0931-7597

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✦ Synopsis

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 can be efficiently halogenated to 2'-halo derivative (VI). This or the 2'-stannylated compound (V) are useful educts for Stille coupling reactions providing various 2'-substituted nucleoside analogues (VIII) and (X). Desilylation of these compounds [cf. (X)] causes no further elimination. -

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