143741-87-1Relevant academic research and scientific papers
The reaction of acetal-type protective groups in combination with TMSOTf and 2,2′-bipyridyl; Mild and chemoselective deprotection and direct conversion to other protective groups
Fujioka, Hiromichi,Minamitsuji, Yutaka,Kubo, Ozora,Senami, Kento,Maegawa, Tomohiro
, p. 2949 - 2960 (2011/05/12)
A mild and chemoselective deprotection method of various acetal-type protective groups, such as MOM, MEM, BOM, and SEM ethers, has been developed. The combination of TMSOTf and 2,2′-bipyridyl was very effective for the deprotection, and the reaction proceeded via the formation of pyridinium intermediates, which were hydrolyzed to the corresponding alcohols in good to high yields. The features of this method are mild (almost neutral) reaction conditions and the tolerability of acid-sensitive functional groups. This method is also applicable for the direct conversion of MOM ether to BOM or SEM ether using the appropriate alcohols instead of H2O.
Remarkable effect of 2,2′-bipyridyl: Mild and highly chemoselective deprotection of methoxymethyl (MOM) ethers in combination with TMSOTf (TESOTf)-2,2′-bipyridyl
Fujioka, Hiromichi,Kubo, Ozora,Senami, Kento,Minamitsuji, Yutaka,Maegawa, Tomohiro
supporting information; experimental part, p. 4429 - 4431 (2009/12/29)
The remarkable effect of 2,2′-bipyridyl led to the successful development of the mild and highly chemoselective deprotection method of methoxymethyl (MOM) ethers using the combination of TMSOTf (or TESOTf) and 2,2′-bipyridyl; this method can be applied to the direct conversion of the MOM group to other ethereal protective groups (e.g. benzyloxymethyl) with the corresponding alcohols. The Royal Society of Chemistry 2009.
An efficient protocol for the preparation of MOM ethers and their deprotection using zirconium(IV) chloride
Sharma,Reddy, K. Laxma,Sree Lakshmi,Radha Krishna, Palakodety
, p. 9229 - 9232 (2007/10/03)
An efficient protocol for the preparation of MOM ethers from alcohols and formaldehyde dimethyl acetal (DMFA) using ZrCl4 (10 mol %) at room temperature under solvent free conditions has been developed. Similarly, the same Lewis acid, ZrCl4 (50 mol %), in isopropanol at reflux was utilised for the deprotection of MOM ethers. An efficient protocol for the preparation of MOM ethers from alcohols and formaldehyde dimethyl acetal (DMFA) using ZrCl4 (10 mol %) at room temperature under solvent free conditions has been developed. Similarly, the same Lewis acid, ZrCl4 (50 mol %), in isopropanol at reflux was utilised for the deprotection of MOM ethers.
Montmorillonite catalysed methoxymethylation of alcohols
Kantam, M. Lakshmi,Santhi, P. Lakshmi
, p. 260 - 261 (2007/10/03)
Montmorillonite is an effective heterogeneous catalyst for the methoxymethylation of alcohols.
