Chemical Properties
Clear Colourless Liquid
Uses
3-(T-butyldimethylsiloxy)propanol is primarily used as a protective group in organic synthesis, specifically for protecting alcohol or phenol functional groups. It can also act as a coupling agent, adhesion promoter, and forms periodic mesoporous silicas.
General Description
3-((
tert-Butyldimethylsilyl)oxy)-propanol (3-[(
tert-butyldimethylsilyl)oxy]-1-propanol) is formed as an intermediate during the synthesis of 3-(
tert-butyldimethylsilyl)oxy]propanal.
Synthesis
The general procedure for the synthesis of 3-(tert-butyldimethylsilyloxy)propanol from tert-butyldimethylchlorosilane and 1,3-propanediol is as follows: this synthesis has been reported in the literature as part of the exemplary "bottom fragment "15 for the preparation of dictyostatin and its analogs. Specifically, 1,3-propanediol is converted in nine steps to the known bis-TBS-protected Homer-Wadsworth-Emmons product by an Evans chirality-assisted method.10 For related literature, see Phukan, P.; Sasmal, S.; Maier, M. E. Eur. J. Org. Chem. 2003, 1733 and Andrus, S., S., S., S., S., S., S., S., S., and S.. 2003, 1733 and Andrus, M. B.; Argade, A. B. Tetrahedron Lett. 1996, 37, 5049.
References
[1] Patent: WO2005/117588, 2005, A2. Location in patent: Page/Page column 31
[2] Journal of the American Chemical Society, 2004, vol. 126, # 37, p. 11440 - 11441
[3] Organic Letters, 2007, vol. 9, # 16, p. 3105 - 3108
[4] Patent: WO2014/145302, 2014, A2. Location in patent: Page/Page column 34; 35; 38; 39
[5] Patent: WO2016/44558, 2016, A1. Location in patent: Page/Page column 51; 52; 54; 55
