反応式
C([O:8][C@@H:9]1[C@@H:14]([O:15]CC2C=CC=CC=2)[C@@H:13]([O:23]CC2C=CC=CC=2)[C@@H:12]([CH2:31][O:32]CC2C=CC=CC=2)[O:11][C@:10]21[C:59]1[C:42](=[CH:43][C:44]3[O:48][N:47]=[C:46]([CH2:49][C:50]4[CH:55]=[CH:54][C:53]([CH2:56][CH3:57])=[CH:52][CH:51]=4)[C:45]=3[CH:58]=1)[CH2:41][O:40]2)C1C=CC=CC=1.CC1C(C)=C(C)C(C)=C(C)C=1.B(Cl)(Cl)Cl.CO>ClCCl>[CH2:56]([C:53]1[CH:54]=[CH:55][C:50]([CH2:49][C:46]2[C:45]3[CH:58]=[C:59]4[C@:10]5([C@H:9]([OH:8])[C@@H:14]([OH:15])[C@H:13]([OH:23])[C@@H:12]([CH2:31][OH:32])[O:11]5)[O:40][CH2:41][C:42]4=[CH:43][C:44]=3[O:48][N:47]=2)=[CH:51][CH:52]=1)[CH3:57]参加物
反応物 4
生成物 1
試薬・触媒・溶媒 1
反応条件
- 温度
- -78 °C
実験手順
(3′R,4′S,5S,5′S,6′R)-3′,4′,5′-tris-benzyloxy-6′-benzyloxymethyl-3-[(4-ethylphenyl)methyl]-3′,4′,5′,6′-tetrahydro-spiro[furo[3,4,f]benzoisoxazole-5(7H),2′-[2H]pyran] (86.9 mg, 0.110 mmol) was dissolved in dichloromethane (3.7 mL). Pentamethylbenzene (0.245 g, 1.65 mmol) was added thereto, and then this solution was cooled to −78° C. A solution of boron trichloride in dichloromethane (1.0 M, 0.55 mL) was added dropwise thereto. The resulting mixture was stirred for 2 hours, and then methanol (2.5 mL) was added thereto. The temperature of the mixture was raised to room temperature. The reaction mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel flash column chromatography (developing solution=methanol:dichloromethane (1:12)), to thereby obtain the titled compound (23.0 mg, 48%).
後処理
- temperatureThe temperature of the mixture was raised to room temperature
- concentrationThe reaction mixture was concentrated under reduced pressure
- customThe resulting residue was purified by silica gel flash column chromatography (developing solution=methanol:dichloromethane (1:12))
出典と根拠
- ORDレコード
- ord-23a20a21e36649748f2e82539f1792ba
- 出典データセット
- uspto-grants-2012_06
- 特許番号
- US08207134B2
関連ノート
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