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20544442423
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8744253714
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6b and more practical for 2a which completes in only 11 steps, however, it requires the commercially available phytosphingosine and is not expandable enough for analogue syntheses including 2b. Preparing commercially unavailable phytosphingosine derivatives for this route must require several additional steps, which makes this route less attractive for SAR purposes
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20544448636
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note
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In this reaction, the starting α-ethynyl-galactopyranose 5 was usually recovered unchanged in over 15% yield.
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29
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20544449124
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note
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3): δ 7.6-7.57 (m, 2H), 7.5-7.2 (m, 23H), 5.66 (dd, 1H, J = 8.9 Hz, 1.8 Hz), 4.90 (d, 1H, J = 11.4 Hz), 4.80 (dd, 1H, J = 6.0 Hz, 1.8 Hz), 4.77 (d, 1H, J = 11.7 Hz), 4.69 (d, 1H, J = 11.7 Hz), 4.68 (d, 1H, J = 11.7 Hz), 4.61 (d, 1H, J = 11.7 Hz), 4.55 (d, 1H, J = 11.4 Hz), 4.45 (d, 1H, J = 11.9 Hz), 4.37 (d, 1H, J = 11.9 Hz), 4.26 (dd, 1H, J = 8.9 Hz, 5.7 Hz), 4.11 (ddd, 1H, J = 13.6 Hz, 5.7 Hz, 3.2 Hz), 4.06 (dd, 1H, J = 9.8 Hz, 5.9 Hz), 3.96 (t, 3H, J = 6.4 Hz), 3.93-3.91 (m, 1H), 3.72 (dd, 1H, J = 9.8 Hz, 2.8 Hz), 3.57 (s, 3H), 3.5-3.4 (m, 2H), 1.75-1.55 (m, 2H), 1.55-1.5 (m, 1H), 1.40 (s, 3H), 1.32 (s, 3H), 1.3-1.1 (m, 5H), 0.81 (t, 3H, J = 6.8 Hz).
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32
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85009579579
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Y. Tamura, H. Annoura, M. Fuji, T. Yoshida, R. Takeuchi, and H. Fujioka Chem. Pharm. Bull. 35 1987 4736 4746
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Tamura, Y.1
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Fuji, M.3
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Takeuchi, R.5
Fujioka, H.6
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34
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20544459281
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note
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The total chemical yield of 10a,b was decreased to 39% with a similar diastereomeric ratio when the magnesium acetylide of 5 was used in this reaction. The zinc acetylide derived from 5 produced only a trace of 10a,b.
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35
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20544461858
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note
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8, 702.5884, found 702.5853.
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36
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20544445147
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note
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The effect of 2b in several animal models of autoimmune disease is currently under investigation and will be reported elsewhere.
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