The example of a silyl-Hilbert-Johnson nucleosidation reaction in Section 25.3 is presumed to involve an intermediate ribosyl

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The example of a silyl-Hilbert-Johnson nucleosidation reaction in Section 25.3 is presumed to involve an intermediate ribosyl cation that is stabilized by intramolecular interactions involving the C2 benzoyl group. This intermediate blocks attack by the heterocyclic base from the a face of the ribose ring but allows attack on the β face, as required for formation of the desired product. Propose a structure for the ribosyl cation intermediate that explains the stereoselective bonding of the base.
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Organic Chemistry

ISBN: 978-1118133576

11th edition

Authors: Graham Solomons, Craig Fryhle, Scott Snyder

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