Selective Acidic Cleavage of Ketals in the Presence oftert-Butyldimethylsilyl Ethers
- 1 October 1995
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 25 (19) , 2959-2962
- https://doi.org/10.1080/00397919508011426
Abstract
Dilute methanolic HCI in anhydrous THF (3OH, ca. 10−2 molar H+) cleaves acetals and ketals, whereas t-butyldimethylsilyl ethers where recovered unchanged even at elevated temperatures.Keywords
This publication has 11 references indexed in Scilit:
- Hypervalent species of silicon: structure and reactivityJournal of Organometallic Chemistry, 1990
- Activation and synthetic applications of thiostannanes. Deprotection and transformations of tetrahydropyranyl ethersThe Journal of Organic Chemistry, 1990
- Chirale Lactole, VII. O,O‐ und O,N‐Acetalbildungsreaktionen der enantiomerenreinen exo‐anellierten Octahydro‐7,8,8‐trimethyl‐4,7‐methanobenzofuran‐2‐ol‐SchutzgruppeEuropean Journal of Inorganic Chemistry, 1988
- Selective removal of tetrahydropyranyl ethers in the presence of tert-butyldimethylsilyl ethers with magnesium bromide in etherTetrahedron Letters, 1987
- A convenient procedure for the monosilylation of symmetric 1,n-diolsThe Journal of Organic Chemistry, 1986
- Dimethylboron bromide and diphenylboron bromide: cleavage of acetals and ketalsThe Journal of Organic Chemistry, 1984
- Selective removal of tetrahydropyranyl ethers in the presence of t-butyldimethylsilyl ethersTetrahedron Letters, 1984
- Simple efficient synthesis of LTB4 and 12-epi-LTB4Tetrahedron Letters, 1982
- Pyridinium p-toluenesulfonate. A mild and efficient catalyst for the tetrahydropyranylation of alcoholsThe Journal of Organic Chemistry, 1977
- Kinetic and stereochemical evidence for nucleophilic assistance in the nucleophilic hydrolysis of chlorosilanesJournal of the Chemical Society, Chemical Communications, 1977