Thiophenol → 1-(Phenylthio)-2-phthalimidyl-1,2-dideoxy-beta-D-glucopyranose triacetate

HRID 613658ノート

反応式

HRID 613658 の反応式
C(O[C@@H:5]1[O:18][C@H:17]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[C@@H:12]([O:13][C:14](=[O:16])[CH3:15])[C@H:7]([O:8][C:9](=[O:11])[CH3:10])[C@H:6]1[N:24]1[C:28](=[O:29])[C:27]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]2[C:25]1=[O:34])(=O)C.B(F)(F)F.CCOCC.[C:44]1([SH:50])[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.C(OCC)(=O)C>ClCCl>[C:9]([O:8][C@H:7]1[C@H:12]([O:13][C:14](=[O:16])[CH3:15])[C@@H:17]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:18][C@@H:5]([S:50][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C@@H:6]1[N:24]1[C:28](=[O:29])[C:27]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]2[C:25]1=[O:34])(=[O:11])[CH3:10]

参加物

6

反応物 4

HCID 7969ThiophenolHCID 8000Boron trifluoride etherateHCID 8857Ethyl AcetateHCID 2728904beta-D-Glucopyranose, 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-, 1,3,4,6-tetraacetate

生成物 1

HCID 110496911-(Phenylthio)-2-phthalimidyl-1,2-dideoxy-beta-D-glucopyranose triacetate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

3.82 g (0.008 Mol) of 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose was dissolved in 80 ml of anhydrous dichloromethane and stirred at 0° C. under an atmosphere of nitrogen. To this solution, 4.0 ml (0.032 Mol) of boron trifluoride diethyl etherate was slowly added. This was followed by 2.2 ml (0.021 Mol) of thiophenol. The resulting solution was stirred at 0° C. for 4 hr. and at RT for 2 hr. and then poured into a mixture of ethyl acetate (500 ml) and ice-cold saturated sodium bicarbonate solution (200 ml).

後処理

  1. stirringThe resulting solution was stirred at 0° C. for 4 hr

出典と根拠

ORDレコード
ord-587becf04bbe4b90a64748b579785dea
出典データセット
uspto-grants-1999_12
特許番号
US06008333

反応ノート

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