Tetrahedron

Solvent-modulated Pd/C-catalyzed deprotection of silyl ethers and chemoselective hydrogenation

T Ikawa, K Hattori, H Sajiki, K Hirota

Index: Ikawa, Takashi; Hattori, Kazuyuki; Sajiki, Hironao; Hirota, Kosaku Tetrahedron, 2004 , vol. 60, # 32 p. 6901 - 6911

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Citation Number: 50

Abstract

Recently we have reported undesirable and frequent deprotection of the TBDMS protective group of a variety of hydroxyl functions occurred under neutral and mild hydrogenation conditions using 10% Pd/C in MeOH. The deprotection of silyl ethers is susceptible to significant solvent effect. TBDMS and TES protecting groups were selectively cleaved in the presence of acid-sensitive functional groups such as TIPS ether, TBDPS ether and ...

~99%

~92%

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~83%

~94%

~45%

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~97%

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~21%

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