Process for synthesis of silyl alcohols

Organic compounds -- part of the class 532-570 series – Organic compounds – Silicon containing

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C07F 708

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051130050

ABSTRACT:
Novel silyl alcohols having bulky substituents bonded to the silicon, and the silyl group attached to a carbon include the preferred 2-silyl-ethan-1-ols. A method for synthesizing silyl substituted alcohols include hydrosilation of a vinylic ester, especially vinyl acetate, followed by hydrolysis in mild base. The silyl alcohols are useful in preparing phosphorylating reagents for phosphorylating an oligonucleotide. The phosphorylated intermediate bearing the silyl group may be separated from failure product on the basis of bulky substituents on the silyl protecting group, which is later removed, e.g. by fluoride ion.

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Honda et al., Tetrahedron Letters, 22(22):2093-2096 (1981).
Lesage et al., J. Org. Chem., 55:5413 (1990).

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