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  • Remarkable effect of 2,2'-bipyridyl: mild and highly chemoselective deprotection of methoxymethyl (MOM) ethers in combination with TMSOTf (TESOTf)-2,2'-bipyridyl.

Remarkable effect of 2,2'-bipyridyl: mild and highly chemoselective deprotection of methoxymethyl (MOM) ethers in combination with TMSOTf (TESOTf)-2,2'-bipyridyl.

Chemical communications (Cambridge, England) (2009-07-15)
Hiromichi Fujioka, Ozora Kubo, Kento Senami, Yutaka Minamitsuji, Tomohiro Maegawa
ABSTRACT

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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Trimethylsilyl trifluoromethanesulfonate, purum, ≥98.0% (T)
Sigma-Aldrich
Trimethylsilyl trifluoromethanesulfonate, 99%