(1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-5-[4-[2-[[[(2-hydroxy-1,1-dimethylethyl)amino]carbonyl]amino]ethyl]benzyl]-4-methylphenyl)-D-glucitol → (1S)-1,5-anhydro-1-[5-[4-[2-[[(2-hydroxy-1,1-dimethylethyl)aminocarbonyl]amino]ethyl]benzyl]-2-hydroxy-4-methylphenyl]-D-glucitol

HRID 1009890ノート

反応式

HRID 1009890 の反応式
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@H:10]1[C:40]1[CH:45]=[C:44]([CH2:46][C:47]2[CH:52]=[CH:51][C:50]([CH2:53][CH2:54][NH:55][C:56]([NH:58][C:59]([CH3:63])([CH3:62])[CH2:60][OH:61])=[O:57])=[CH:49][CH:48]=2)[C:43]([CH3:64])=[CH:42][C:41]=1[O:65]CC1C=CC=CC=1)C1C=CC=CC=1>[OH-].[Pd+2].[OH-].CO>[OH:61][CH2:60][C:59]([NH:58][C:56]([NH:55][CH2:54][CH2:53][C:50]1[CH:51]=[CH:52][C:47]([CH2:46][C:44]2[C:43]([CH3:64])=[CH:42][C:41]([OH:65])=[C:40]([C@@H:10]3[O:11][C@H:12]([CH2:31][OH:32])[C@@H:13]([OH:23])[C@H:14]([OH:15])[C@H:9]3[OH:8])[CH:45]=2)=[CH:48][CH:49]=1)=[O:57])([CH3:62])[CH3:63]

参加物

4

反応物 1

HCID 86638449(1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-5-[4-[2-[[[(2-hydroxy-1,1-dimethylethyl)amino]carbonyl]amino]ethyl]benzyl]-4-methylphenyl)-D-glucitol

生成物 1

HCID 67304774(1S)-1,5-anhydro-1-[5-[4-[2-[[(2-hydroxy-1,1-dimethylethyl)aminocarbonyl]amino]ethyl]benzyl]-2-hydroxy-4-methylphenyl]-D-glucitol収率 58%

試薬・触媒・溶媒 2

HCID 9942167Palladium hydroxide触媒HCID 887Methanol溶媒

実験手順

To a methanol solution (4 mL) of (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-5-[4-[2-[[[(2-hydroxy-1,1-dimethylethyl)amino]carbonyl]amino]ethyl]benzyl]-4-methylphenyl]-D-glucitol (0.184 mg, 0.190 mmol) was added 20% palladium hydroxide (0.180 g), and the mixture was stirred under a hydrogen atmosphere at room temperature overnight. The reaction solution was filtered through celite and evaporated under reduced pressure. Thus obtained residue was purified with silica gel column chromatography (chloroform:methanol=17:3) to obtain the title compound (57 mg, 58%) as a colorless powder. NMR data and MS data of the compound are shown in Table 1.

後処理

  1. filtrationThe reaction solution was filtered through celite
  2. customevaporated under reduced pressure
  3. customThus obtained residue was purified with silica gel column chromatography (chloroform:methanol=17:3)

出典と根拠

ORDレコード
ord-77ec8803dd5d4dc1aee73390bd751539
出典データセット
uspto-grants-2011_07
特許番号
US07973012B2

反応ノート

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