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Synthesis and Reactivity of a Stable Nitrile Imine by Ghislaine. Sicard; Antoine. Baceiredo; Guy. Bertrand is a Chemistry article available to read on EtoBox.

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3) The result with 14b (Table I, entry iii) indicates that of the three acetals (benzylic, a-ethoxyethyl, and glycosidic) present in the molecule, only the last was removed during brominolysis. By contrast, upon treatment of 14b with mild acid, the last was the only acetal to survive-as expected. (4) Pursuant to the survival of the acid labile protecting groups, the result with the silyl ether 14c (entry iv) should be noted. In general, the results with 14b -14g reveal that under the deglycosidation conditions, the benzylidene ring does not undergo the well-known H a n e ~s i a n -H u l l a r ' ~\* ~~ reaction with NBS, a procedure widely used to cleave a benzylidene acetal while leaving a glycosidic center intact The formation of 15b -15g allows that pattern of chemoselectivity to be reversed. ( 5 ) In view of the reactions in entry i, survival of the 0-benzyl ethers in entry v ( 1 4 -15d) is not surprising. However, the oxidative conditions proved to be so mild that even the activated methoxybenzyl ether survived (14e -1%) to a substantial degree (entry vi). (6) The results with the diacetate 14f (entry vii) were complicated by acetyl migration to give 16. (In this context, it sh

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Author

Ghislaine. Sicard; Antoine. Baceiredo; Guy. Bertrand

Publisher

American Chemical Society; American Chemical Society (ACS); Research Square (ISSN 0002-7863)

Published

1988

Language

EN

Field

Chemistry (Physical Sciences)