Potassium Bromide → HCID 11453970, Verbindung

HRID 1677839Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1677839
[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

Komponenten

4

Edukt 2

HCID 253877Potassium BromideHCID 49864734HCID 49864734, Verbindung2×

Produkt 1

HCID 11453970HCID 11453970, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-021e1168960a4313a71ccd01822f1810
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008346B2

Notizen zur Reaktion

Wird geladen…