Tuesday, September 13, 2011

Acronym in chemistry: BIBS for di-tert-butylisobutylsilyl, a protecting group

Di-tert-butylisobutylsilyl, abbreviated as BIBS, is a sterically bulk trialkylsily protecting group. BIBS is useful for protecting acidic hydroxyl molecules such as those of trifluoromethanesulfonic acid (triflic acid, HTf), giving the silyl ether compound di-tert-butylisobutyl silyl triflate (BIBSOTf). The intermediate may then be deprotected with tetrabutylammonium fluoride. The BIBS protecting group offers new routes in synthetic chemistry by obtaining robust protected moieties via Si-O and Si-N bonds. BIBS' bulkiness retards or inhibits hydrolysis in comparison with other commonly employed protecting groups [1,2].

A CurlySMILES notation for BIBS:

Keywords: organic chemistry, organic synthesis, trialkylsilyl group, structural unit, substructure

[1] Science & Technology Concentrates: A More Stable Silyl Ether. Chemical & Engineering News July 25, 2011, 89 (30), page 38.
[2 ] H. Liang, L. Hu and E. J. Corey: Di-tert-butylisobutylsilyl, Another Useful Protecting Group.Org. Lett. 2011, 13 (15), pp.4120-4123. DOI: 10.1021/ol201640y.

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