JP4945823B2 - 光学活性ビニルケトン誘導体およびこれを用いた光学活性アミノジオール類の製造方法 - Google Patents
光学活性ビニルケトン誘導体およびこれを用いた光学活性アミノジオール類の製造方法 Download PDFInfo
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- JP4945823B2 JP4945823B2 JP2005024063A JP2005024063A JP4945823B2 JP 4945823 B2 JP4945823 B2 JP 4945823B2 JP 2005024063 A JP2005024063 A JP 2005024063A JP 2005024063 A JP2005024063 A JP 2005024063A JP 4945823 B2 JP4945823 B2 JP 4945823B2
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- optically active
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- vinyl ketone
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- 0 *N[C@@](CO*)C(C=C)=* Chemical compound *N[C@@](CO*)C(C=C)=* 0.000 description 1
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
P. Herold, Helv. "Chim. Acta", 71, p.354-p.361 (1988). T. Ibuka, H. Habashita, A. Otaka, N. Fujii, Y. Oguchi, T. Uyehara, and Y. Yamamoto, "J. Org. Chem"., 56, p.4370-p.4382 (1991). P. A. Evans, A. B. Holmes, and K. Russell, "J. Chem. Soc. Perken Trans". 1, 23, p.3397-p.3409, (1994). I. Ojima and E. S. Vidal, "J. Org. Chem"., 63, p.7999-p.8003 (1998).
以下、本発明を実施例によりさらに具体的に説明する。
1H NMR (CDCl3, 400MHz) δ: 6.55 (dd, J = 17.3, 10.7 Hz, 1H), 6.33 (dd, J = 17.3, 1.5 Hz, 1H), 5.82 (d, J = 5.8 Hz, 1H), 5.45-5.55 (brm, 1H), 4.58 (ddd, J = 7.6, 3.7, 3.7 Hz, 1H), 3.99 (dd, J = 10.3, 3.4 Hz, 1H), 3.84 (dd, J = 10.3, 4.4 Hz, 1H), 1.43 (s, 9H), 0.83 (s, 9H), 0.00 (s, 3H), -0.01 (s, 3H)
13C NMR (CDCl3, 100MHz) δ: 170.6, 155.0, 133.0, 128.9, 79.3, 63.1, 59.3, 28.0, 25.4, 17.9, -5.9
1H NMR (CDCl3, 400MHz) δ: 5.91 (ddd, J = 17.3, 10.5, 4.9 Hz, 1H), 5.38 (ddd, J = 17.1, 1.7, 1.7 Hz, 1H), 5.24 (ddd, J = 10.5, 1.7, 1.7 Hz, 1H), 5.21-5.29 (brm, 1H), 4.26 (m, 1H), 3.93 (dd, J = 10.5, 2.9 Hz, 1H), 3.76 (m, 1H), 3.63 (m, 1H), 3.39-3.46 (brm, 1H), 1.45 (s, 9H), 0.90 (s, 9H), 0.06 (s, 3H), 0.07 (s, 3H)
13C NMR (CDCl3, 100MHz) δ: 155.7, 137.8, 115.7, 79.3, 74.3, 63.0, 54.2, 28.2, 25.6, 18.0, -5.5, -5.8
1H NMR (CDCl3, 400MHz) δ: 6.57 (dd, J= 10.5, 17.3 Hz, 1H ), 6.44 (dd, J= 1.5, 17.3 Hz, 1H ), 5.93 (dd, J= 10.5, 0.7 Hz, 1H ), 5.69 (brm, 1H), 4.66 (m, 1H), 3.95 (ddd, J= 11.5, 6.8, 3.7 Hz, 1H ), 3.90 (ddd, J= 11.5, 5.4, 4.4 Hz, 1H ), 2.75 (brm, 1H), 1.46 (s, 9H)
13C NMR (CDCl3, 100MHz) δ: 170.6, 155.6, 132.6, 129.7, 79.6, 62.3, 59.5, 27.9
1H NMR (CDCl3, 400MHz) δ: 5.91 (ddd, J = 17.3, 10.5, 4.9 Hz, 1H), 5.38 (ddd, J = 17.1, 1.7, 1.7 Hz, 1H), 5.24 (ddd, J = 10.5, 1.7, 1.7 Hz, 1H), 5.21-5.29 (brm, 1H), 4.26 (m, 1H), 3.93 (dd, J = 10.5, 2.9 Hz, 1H), 3.76 (m, 1H), 3.63 (m, 1H), 3.39-3.46 (brm, 1H), 1.45 (s, 9H), 0.90 (s, 9H), 0.06 (s, 3H), 0.07 (s, 3H)
13C NMR (CDCl3, 100MHz) δ: 155.7, 137.8, 115.7, 79.3, 74.3, 63.0, 54.2, 28.2, 25.6, 18.0, -5.5, -5.8
1H NMR (CDCl3, 400MHz) δ: 5.75 (dtd, J= 15.4, 6.8, 1.2 Hz, 1H), 5.50 (ddt, J= 15.4, 5.6, 1.5 Hz, 1H), 5.23 (brm, 1H), 4.27 (m, 1H), 3.93 (dd, J= 10.2, 2.9 Hz, 1H), 3.75 (dd, J= 10.5, 2.4 Hz, 1H), 3.57 (m, 1H), 3.31 (brm, 1H), 2.05 (dt, J= 7.1, 7.1 Hz, 2H), 1.45 (s, 9H), 1.25 (s, 22H), 0.90 (s, 9H), 0.85 (m, 3H), 0.06 (s, 6H)
13C NMR (CDCl3, 100MHz) δ: 155.4, 133.1, 129.4, 79.4, 74.6, 63.4, 54.5, 32.3, 31.9, 29.7, 29.5, 29.3, 29.2, 28.4, 28.3, 25.8, 22.7, 18.1, 14.1, -5.6
1H NMR (CD3OD, 400MHz) δ: 5.67 (dt, J = 14.9, 6.8 Hz, 1H), 5.39 (ddm, J = 15.4, 7.3 Hz, 1H), 3.98 (m, 1H), 3.62 (m, 1H), 3.45 (dd, J = 11.0, 7.3 Hz, 1H), 2.80 (m, 1H), 1.99 (m, 2H), 1.32 (m, 2H), 1.26 - 1.17 (m, 20H), 0.80 (t, J = 7.1 Hz, 3H)
13C NMR (CD3OD, 100MHz) δ: 135.6, 130.1, 73.8, 62.8, 58.1, 33.4, 33.1, 30.9, 30.79, 30.75, 30.6, 30.5, 30.35, 30.32, 23.7, 14.5
1H NMR (CDCl3, 400MHz) δ: 6.28 (brd, J = 6.8 Hz, 1H), 5.78 (dt, J = 15.4, 6.8 Hz, 1H), 5.53 (dd, J = 15.4, 6.3 Hz, 1H), 4.31 (m, 1H), 3.95 (dd, J = 11.0, 3.7 Hz, 1H), 3.90 (m, 1H), 3.70 (dd, J = 11.0, 2.7 Hz, 1H), 2.93 (brs, 2H), 2.23 (t, J = 7.6 Hz, 2H), 2.06 (m, 2H), 1.64 (tt, J = 7.1, 7.1 Hz, 2H), 1.40 - 1.26 (m, 46H), 0.88 (t, J = 6.8 Hz, 6H)
13C NMR (CDCl3, 100MHz) δ: 174.0, 134.2, 128.8, 74.6, 62.5, 54.5, 36.8, 32.3, 31.9, 29.69, 29.65, 29.5, 29.35, 29.29, 29.23, 29.1, 25.8, 22.7, 14.1
Claims (3)
- 前記アルミニウム還元剤がリチウム(トリtert-ブトキシ)アルミノヒドリドであることを特徴とする請求項2記載の光学活性アミノジオール類の製造方法。
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JP2005024063A JP4945823B2 (ja) | 2005-01-31 | 2005-01-31 | 光学活性ビニルケトン誘導体およびこれを用いた光学活性アミノジオール類の製造方法 |
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JP2005024063A JP4945823B2 (ja) | 2005-01-31 | 2005-01-31 | 光学活性ビニルケトン誘導体およびこれを用いた光学活性アミノジオール類の製造方法 |
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JP2006206546A JP2006206546A (ja) | 2006-08-10 |
JP4945823B2 true JP4945823B2 (ja) | 2012-06-06 |
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