Benzoic anhydride → 10-benzoyl-10deacetylbaccatin III

HRID 363845

反応式

HRID 363845 の反応式
[CH3:1][C:2]1[C@@H:19]([OH:20])[CH2:18][C@:14]2([OH:21])[C:15]([CH3:17])([CH3:16])[C:3]=1[C@@H:4]([OH:39])[C:5]([C@@:7]1([CH3:38])[C@H:12]([C@@H:13]2[O:22][C:23]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:24])[C@:11]2([O:33][C:34]([CH3:36])=[O:35])[CH2:31][O:32][C@@H:10]2[CH2:9][C@@H:8]1[OH:37])=[O:6].[C:40](OC(=O)C1C=CC=CC=1)(=[O:47])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.O.FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O.C(Cl)Cl.CO>O1CCCC1>[CH3:1][C:2]1[C@@H:19]([OH:20])[CH2:18][C@:14]2([OH:21])[C:15]([CH3:16])([CH3:17])[C:3]=1[C@@H:4]([OH:39])[C:5]([C@@:7]1([CH3:38])[C@H:12]([C@@H:13]2[O:22][C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:24])[C@:11]2([O:33][C:34]([CH3:36])=[O:35])[CH2:31][O:32][C@@H:10]2[CH2:9][C@@H:8]1[OH:37])=[O:6].[CH3:1][C:2]1[C@@H:19]([OH:20])[CH2:18][C@:14]2([OH:21])[C:15]([CH3:16])([CH3:17])[C:3]=1[C@@H:4]([O:39][C:40]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:47])[C:5]([C@@:7]1([CH3:38])[C@H:12]([C@@H:13]2[O:22][C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:24])[C@:11]2([O:33][C:34]([CH3:36])=[O:35])[CH2:31][O:32][C@@H:10]2[CH2:9][C@@H:8]1[OH:37])=[O:6]

参加物

7

反応物 4

HCID 7167Benzoic anhydrideHCID 15427210-deacetylbaccatin IIIHCID 21226129Dichloromethane methanolHCID 45075687Ytterbium(3+) trifluoromethanesulfonate--water (1/3/1)

生成物 2

HCID 15427210-deacetylbaccatin III収率 22%HCID 1554999310-benzoyl-10deacetylbaccatin III収率 62%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 50 mg (91.9 μmol) of 10-deacetylbaccatin III and 13 μL (1.5 eq.) of benzoic anhydride in 2.0 mL of freshly distilled tetrahydrofuran 100 μL of a solution of 5.8 mg of commercial ytterbium trifluoromethanesulfonate hydrate in 1.0 mL of tetrahydrofuran was added. The reaction mixture was stirred at room temperature for 48 hours. Usual workup and isolation of the product by means of preparative TLC (Silica 60, CH2Cl2/MeOH 10:1) afforded 11 mg unreacted 10-deacetylbaccatin III (22%) along with 29 mg of 10-benzoyl-10deacetylbaccatin III (62%), m.p. 154°-156° C. C36H40O11 calculated C 66.66% H 6.22% measured C 66.50% H 6.23%. 1H-NMR (300 MHz, CDCl3) δ (ppm)=1.18 (s, 3H), 1.25 (s, 3H), 1.69 (s, 3H), 1.80-1.93 (m, 1H), 2.09 (s, 3H), 2.16-2.23 (m, 2H), 2.29 (s, 3H), 2.53-2.61 (m, 1H), 3.95 (d, 1H, J=6.9), 4.17 (d, 1H, J=8.3), 4.32 (d, 1H, J=8.3), 4.55 (dd, 1H, J=6.6, 10.6), 4.91 (br t, 1H, J=7.9), 5.00 (d, 1H, J=9.2), 5.67 (d, 1H, J=6.9), 6.59 (s, 1H), 7.40-7.52 (m, 4H), 7.54-7.61 (m, 2H), 8.04-8.14 (m, 4H).

出典と根拠

ORDレコード
ord-1a9cc81b4efa48e3adb222b2b96ff47b
出典データセット
uspto-grants-1999_02
特許番号
US05874595

関連ノート

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