Propionic anhydride → (3S,4aR,4bS,6S,8R,8aR,10aR)-3-Furan-3-yl-6-isobutyryloxy-4a,8a-dimethyl-1,5-dioxo-dodecahydro-2-oxa-phenanthrene-8-carboxylic acid methyl ester

HRID 12314

反応式

HRID 12314 の反応式
C(OC(=O)CC)(=O)CC.[CH3:10][O:11][C:12]([C@@H:14]1[CH2:27][C@H:26]([OH:28])[C:25](=[O:29])[C@H:24]2[C@@:15]1([CH3:37])[CH2:16][CH2:17][C@H:18]1[C@:23]2([CH3:30])[CH2:22][C@@H:21]([C:31]2[CH:35]=[CH:34][O:33][CH:32]=2)[O:20][C:19]1=[O:36])=[O:13].[C:38](Cl)(=[O:42])[CH:39]([CH3:41])[CH3:40]>>[CH3:10][O:11][C:12]([C@@H:14]1[CH2:27][C@H:26]([O:28][C:38](=[O:42])[CH:39]([CH3:41])[CH3:40])[C:25](=[O:29])[C@H:24]2[C@@:15]1([CH3:37])[CH2:16][CH2:17][C@@H:18]1[C@:23]2([CH3:30])[CH2:22][C@@H:21]([C:31]2[CH:35]=[CH:34][O:33][CH:32]=2)[O:20][C:19]1=[O:36])=[O:13]

参加物

4

反応物 3

HCID 31263Propionic anhydrideHCID 62325Isobutyryl chlorideHCID 11395172(2S,4aS,6aR,7R,9S,10aS,10bR)-9-(hydroxy)-2-(3-furanyl)dodecahydro-6a,10b-dimethyl-4,10-dioxo-2H-naphtho[2,1-c]pyran-7-carboxylic acid methyl ester

生成物 1

HCID 11419799(3S,4aR,4bS,6S,8R,8aR,10aR)-3-Furan-3-yl-6-isobutyryloxy-4a,8a-dimethyl-1,5-dioxo-dodecahydro-2-oxa-phenanthrene-8-carboxylic acid methyl ester収率 62%

実験手順

Using a procedure similar to that described in Example 4 except replacing the propionic anhydride used therein with the requisite anhydride, the title compound 10 (0.04 g, 62%) was prepared as a white solid, mp 209-211° C.; 10 was synthesized as described for 9 from 8a using isobutyryl chloride to afford 0.04 g (62%) of 10 as a white solid, mp 209-211° C.; 1H NMR (CDCl3): δ 1.13 (3H, s, H-19); 1.24 (3H, d, J=6.9 Hz, CH3CH(CH3)CO2); 1.26 (3H, d, J=6.9 Hz CH3CH(CH3)CO2,); 1.46 (3H, s, H-20); 1.52-1.78 (3H, m, H-7α,β and H-11β); 1.80 (1H, ddd, J=3.0, 3.0, 9.9 Hz, H-6α); 2.12 (2H, m, H-3α and H-8); 2.20. (1H, s, H-10); 2.25-2.35 (2H, m, H-3β and H-6β); 2.51 (1H, dd, J=5.1, 13.2 Hz, H-11α); 2.68 (1H, sept, J=6.9 Hz, CH3CH(CH3)CO2); 2.77 (1H, dd, J=8.4, 8.4 Hz, H-4); 3.74 (3H, s, CO2CH3); 5.15 (1H, dd, J=9.9, 10.3 Hz, H-2); 5.52 (1H, dd, J=5.3, 11.9 Hz, H-12); 6.39 (1H, dd, J=0.9, 1.5 Hz, H-14); 7.40 (1H, dd, J=1.5, 1.5 Hz, H-15); 7.42 (1H, dd, J=0.9, 1.5 Hz, H-16).

後処理

  1. custom10 was synthesized

出典と根拠

ORDレコード
ord-8cf51e6dc1724239bb5526d1cc06716b
出典データセット
uspto-grants-2010_06
特許番号
US07728001B2

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