참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | 2,4,6-Trimethylpyridine | HCID 7953 | — |
| 반응물 | Triethylsilyl trifluoromethanesulphonate | HCID 2733308 | — |
| 반응물 | (2R,3S)-2-Methyl-3-propyloxiranemethanol | HCID 10931464 | — |
| 반응물 | (2R,3R)-3-[t-Butyldimethylsilyloxy)-2-methylhexanal | HCID 14959487 | — |
| 생성물 | (2S,3S)-3-(Triethylsilyloxy)-2-methylhexanal | HCID 57173492 | — |
반응 단계
Epoxy alcohol 13, 1.4 eq TESOTf, and 1.5 eq of collidine were reacted as in the preparation of 16 to give 95%+yield (<20:1 de) of crude aldehyde 22 which was chromatographed (SiO2, 3% EtOAc/96% Hex/1% TEA) to give 85% of 22. 1H NMR (CDCl3, 500.135 MHz) δ:9.68 (1H, d, J=2.37 Hz), 3.89 (1H, q, J=5.03 Hz), 2.43 (1H, qdd, J=6.95, 5.03, 2.30 Hz), 1.5-1.2 (4H, m), 1.02 (3H, d, J=6.95 Hz), 0.89 (6H, t J=8.0 Hz), 0.85 (3H, t, J=7.14 Hz), and 0.54 (9H, q, J=7.80 Hz). 13C NMR (CDCl3, 90.55 MHz) δ:205.1, 73.3, 51.3, 37.2, 18.1, 14.1, 10.3, 6.4, and 5.1. IR (thin film): 2957 (s), 2938 (s), 2912 (s), 2877 (s), 1726 (s), 1459 (s), 1415 (w), 1379 (w), 1239 (m), 1155 (w), 1074 (s), 1038 (m), 1005 (w), and 741 (s) cm-1. high resolution MS (m/z): 215. 1467, calcd for C11H23O2Si 215.1467 (M-C2H5). [α]D =+14.7° (c=1.89, CH2Cl2). 1H NMR integration of δ 9.69 to δ 9.72 indicated a 90.3:9.7 ratio.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US05426206 |
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| 출처 데이터셋 | uspto-grants-1995_06 |
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| ORD ID | ord-c0eea5001b34473399159c7a300f0f4d |
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| 출처 메모 | uspto-grants-1995_06 |
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