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Chloroform → (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[5-[4-(2-aminoethyl)benzyl]-2-(benzyloxy)-4-methylphenyl]-D-glucitol

HRID 1009868
ノート
印刷プレビュー

反応式

HRID 1009868 の反応式
C(Cl)(Cl)Cl.[CH2:5]([O:12][C@@H:13]1[C@@H:18]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@H:17]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C@@H:16]([CH2:35][O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[O:15][C@H:14]1[C:44]1[CH:49]=[C:48]([CH2:50][C:51]2[CH:56]=[CH:55][C:54]([CH2:57][CH2:58][NH:59]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)=[CH:53][CH:52]=2)[C:47]([CH3:79])=[CH:46][C:45]=1[O:80][CH2:81][C:82]1[CH:87]=[CH:86][CH:85]=[CH:84][CH:83]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.FC(F)(F)C([O-])=O>C(O)C>[CH2:5]([O:12][C@@H:13]1[C@@H:18]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C@H:17]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C@@H:16]([CH2:35][O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[O:15][C@H:14]1[C:44]1[CH:49]=[C:48]([CH2:50][C:51]2[CH:52]=[CH:53][C:54]([CH2:57][CH2:58][NH2:59])=[CH:55][CH:56]=2)[C:47]([CH3:79])=[CH:46][C:45]=1[O:80][CH2:81][C:82]1[CH:83]=[CH:84][CH:85]=[CH:86][CH:87]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6212ChloroformHCID 84468TrifluoroacetateHCID 86638440(1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-4-methyl-5-[4-[2-(tritylamino)ethyl]benzyl]phenyl]-D-glucitol

生成物 1

HCID 67303921(1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[5-[4-(2-aminoethyl)benzyl]-2-(benzyloxy)-4-methylphenyl]-D-glucitol収率 103.1%

試薬・触媒・溶媒 1

HCID 702
Ethanol
溶媒

実験手順

To a chloroform solution of (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-4-methyl-5-[4-[2-(tritylamino)ethyl]benzyl]phenyl]-D-glucitol (0.402 g, 0.336 mmol) was added at room temperature trifluoroacetate (0.5 mL), and the mixture was stirred for 3 hours at the same temperature. To the reaction solution was added ethanol and then the solvent was evaporated under reduced pressure. Thus obtained residue was purified with NH type silica gel column chromatography (hexane:ethyl acetate=4:6, chloroform:methanol=20:1) to obtain the title compound (0.296 g, quant.) as a colorless oily compound.

後処理

  1. customthe solvent was evaporated under reduced pressure
  2. customThus obtained residue was purified with NH type silica gel column chromatography (hexane:ethyl acetate=4:6, chloroform:methanol=20:1)

出典と根拠

ORDレコード
ord-efedbf8244ce459eba960521bc053ea1
出典データセット
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07973012B2

反応ノート

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