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Tetrabutylammonium Fluoride → (2R,3R,4S,5R)-2-{2-(2-Aminoethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol

HRID 2268350
ノート
印刷プレビュー

反応式

HRID 2268350 の反応式
[NH2:1][CH2:2][CH2:3][C:4]1[N:12]=[C:11]2[C:7]([N:8]=[CH:9][N:10]2[C@H:13]2[C@H:17]([O:18][Si](C(C)(C)C)(C)C)[C@H:16]([O:26][Si](C(C)(C)C)(C)C)[C@@H:15]([CH2:34][O:35][CH3:36])[O:14]2)=[C:6]([NH:37][CH2:38][CH:39]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[N:5]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[NH2:1][CH2:2][CH2:3][C:4]1[N:12]=[C:11]2[C:7]([N:8]=[CH:9][N:10]2[C@H:13]2[C@H:17]([OH:18])[C@H:16]([OH:26])[C@@H:15]([CH2:34][O:35][CH3:36])[O:14]2)=[C:6]([NH:37][CH2:38][CH:39]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[N:5]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 69534061N-{2-(2-Aminoethyl)-9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-9H-purin-6-yl}-N-(2,2-diphenylethyl)amine

生成物 1

HCID 9957801(2R,3R,4S,5R)-2-{2-(2-Aminoethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol収率 103.2%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒
2 回

実験手順

N-{2-(2-Aminoethyl)-9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-9H-purin-6-yl}-N-(2,2-diphenylethyl)amine (1.07 g, 1.46 mmol) (preparation 18) was dissolved in dry tetrahydrofuran (4 ml), a 1M solution of tetra-n-butylammonium fluoride in tetrahydrofuran (6 ml, 6 mmol) added and the mixture stirred at room temperature for 2.5 hr. The solvent was removed under reduced pressure and the residue dissolved in dichloromethane. The solvent was again removed under reduced pressure and the residue purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol:ammonia (90:10:1), to give the product as a foam (760 mg). MS: 505 (MH+).

後処理

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue dissolved in dichloromethane
  3. customThe solvent was again removed under reduced pressure
  4. customthe residue purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol:ammonia (90:10:1)

出典と根拠

ORDレコード
ord-c45bc8cfff1a410193ac5d6d7121f007
出典データセット
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06326359B1

反応ノート

読み込み中…

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