Potassium Bromide → HCID 11453970、化合物

HRID 1677839ノート

反応式

HRID 1677839 の反応式
[K+].[Br-].[CH3:3][C@@H:4]1[C:33]([CH3:35])([CH3:34])[O:32][C@:6]2([O:10][C@H:9]3[CH2:11][C@H:12]4[C@@H:18]5[CH2:19][CH2:20][C@H:21]6[CH2:26][C@H:25]([OH:27])[CH2:24][CH2:23][C@:22]6([CH3:28])[C@H:17]5[C:15](=[O:16])[CH2:14][C@:13]4([CH3:29])[C@H:8]3[C@:7]2([OH:31])[CH3:30])[CH2:5]1>C(Cl)(Cl)Cl>[CH3:3][C@@H:4]1[C:33]([CH3:34])([CH3:35])[O:32][C@@:6]2([O:10][C@H:9]3[CH2:11][C@H:12]4[C@@H:18]5[CH2:19][CH2:20][C@H:21]6[CH2:26][C@H:25]([OH:27])[CH2:24][CH2:23][C@:22]6([CH3:28])[C@H:17]5[C:15](=[O:16])[CH2:14][C@:13]4([CH3:29])[C@H:8]3[C@:7]2([OH:31])[CH3:30])[CH2:5]1

参加物

4

反応物 2

HCID 253877Potassium BromideHCID 49864734HCID 49864734、化合物2 回

生成物 1

HCID 11453970HCID 11453970、化合物

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

colorless crystals, mp: 240° C.; [α]D24−38.0° (c 2.41, CHCl3); 1H NMR (CDCl3) δ 5.31 (s, 1H), 5.00 (brs 1 H), 4.53 (q, J=7 Hz, 1H), 4.24 (brs 1H), 2.69 (dd, J=14.5, 3.5 Hz, 1H), 2.61 (d, J=6.5 Hz, 1H), 2.28 (m, 1H), 2.12 (m, 1H), 2.06 (m, 1H), 2.04 (s, 3H), 1.87 (m, 1H), 1.82 (m, 2H), 1.74 (m, 1H), 1.71 (m, 2H), 1.64 (m, 1H), 1.61 (dd, J=14.5, 4 Hz, 1H), 1.48 (m, 3H), 1.41 (s, 3H), 1.41 (m, 1H), 1.34 (m, 1H), 1.29 (s, 3H), 1.27 (m, 1H), 1.18 (m, 2H), 1.00 (s, 3H), 096 (s, 3H), 0.93 (d, J=7 Hz, 3H), 0.79 (m, 1H); 13C NMR (CDCl3) δ 170.6 s, 117.9 s, 101.3 d, 90.7 s, 84.7 s, 80.6 d, 70.0 d, 66.0 d, 64.3 d, 58.5 d, 56.1 s, 56.0 d, 41.1 d, 40.5 d, 39.2 t, 38.7 t, 35.9 s, 32.4 t, 33.7 t, 32.1 t, 32.1 t, 31.0 d, 29.0 q, 27.4 t, 25.6 t, 22.8 q, 21.4 q, 19.6 q, 14.4 q, 13.9 q; positive NOEs: H-6β/H-8, H-8/H-18, H-12β/H-21, H-12α/H-16, H-14/H-16, H-15β/H-18, H-16/H-17, H-17/H-21, and H-21/H-23α; IR (KBr) 3470, 3300, 1730, 1240 cm−1; EIMS m/z 500 (M−H2O), 485 (4), 442 (4), 372 (100%). The stereochemistry at C-18 was elucidated to be R configuration by positive NOEs between the proton pairs: H-18/H-8 and H-18/H-15β.

後処理

  1. custom39.2 t, 38.7 t, 35.9 s, 32.4 t, 33.7 t, 32.1 t, 32.1 t, 31.0 d, 29.0 q, 27.4 t, 25.6 t, 22.8 q, 21.4 q, 19.6 q, 14.4 q, 13.9 q

出典と根拠

ORDレコード
ord-021e1168960a4313a71ccd01822f1810
出典データセット
uspto-grants-2011_08
特許番号
US08008346B2

反応ノート

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