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Diisopropylethylamine → (2S,3S)-3-(t-Butyldimethylsilyloxy)-2-methylhexanal
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Diisopropylethylamine | HCID 81531 | — |
| 反応物 | tert-Butyldimethylsilyl trifluoromethanesulphonate | HCID 123564 | — |
| 反応物 | (2R,3S)-2-Methyl-3-propyloxiranemethanol | HCID 10931464 | — |
| 反応物 | (2R,3R)-3-[t-Butyldimethylsilyloxy)-2-methylhexanal | HCID 14959487 | — |
| 生成物 | (2S,3S)-3-(t-Butyldimethylsilyloxy)-2-methylhexanal | HCID 10879364 | — |
反応手順
Epoxy alcohol 13, 1.25 eq TBSOTf, and 1.30 eq DIPEA were reacted as in the preparation of 16 to give the crude aldehyde 14 in 95% +yield. 1H NMR, 13C NMR, IR, and high resolution MS are identical to 16. [δ]D=+19.3° (c=1.10, CH2Cl2). 1H NMR integration of δ 9.67 and the contaminating diastereromer at δ 9.71 indicated a >50:1 ratio.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US05426206 |
| 出典データセット | uspto-grants-1995_06 |
| ORD ID | ord-5cf56b8424ec43e3b8980dfd92998226 |
| 出典メモ | uspto-grants-1995_06 |