Atahualpa Pinto

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Organization: Syracuse University
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Co-reporter:Burkhardt I. Wilke, Mark H. Dornan, Jon Yeung, Christopher N. Boddy, Atahualpa Pinto
Tetrahedron Letters 2014 Volume 55(Issue 16) pp:2600-2602
Publication Date(Web):16 April 2014
DOI:10.1016/j.tetlet.2014.02.067
Symmetric diols are useful compounds in the synthesis of natural products, their value often dependent on their successful monoprotection. A general and simple method for the monosilylation of symmetrical primary and secondary diols is reported. The method exploits the solubility differential of diols and their monosilylated counterparts in a binary hexanes/acetonitrile solvent system.Graphical abstract
4,7,10-Trioxa-3-siladodecan-12-ol, 2,2,3,3-tetramethyl-
1-Nonanol, 9-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-
1-Heptanol, 7-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-
1-Propanol, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methyl-
1-Propanol, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2,2-dimethyl-
2-Hexanol, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, (R*,S*)-(±)-
1-Pentanol, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-
4,12-DIOXA-3,13-DISILAPENTADECANE, 2,2,3,3,13,13,14,14-OCTAMETHYL-
ACETONITRILE