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Short Paper | Special issue | Vol 97, No. 1, 2018, pp.574-579
Published online, 17th April, 2018
DOI: 10.3987/COM-18-S(T)32
A New Method of Deuterium Incorporation to TMS-Epoxyalcohol Using Sodium Methylsulfinylmethylide-d5 (NaDMSO-d5)

Yutaro Nanba, Shuhei Tanabe, and Yuichi Kobayashi*

*Department of Biomolecular Engineering, Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, Box B52, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan


A reaction of 1-TMS-1,2-epoxyoctan-3-ol with NaDMSO-d5 (Na+ CD3S(O)CD2), prepared in situ from DMSO-d6 and NaH, afforded non-1-ene-1,1-d2-3,4-diol. Both the anti and syn isomers showed similar reactivity and the stereochemistry was preserved. α-Ethoxyethyl ether of the epoxy alcohol was converted to the corresponding mono-ethoxyethyl ether of the 1-ene-3,4-diol. Hydroboration and hydrogenation of the corresponding TBS ethers afforded compounds with the "CH2CD2OH" and "CH2CD2H" groups, respectively.