Water → N,N'-Bis[4-[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl)-beta-D-glucopyranosylthio]phenyl]octanediamide

HRID 434740

反応式

HRID 434740 の反応式
[C:1]([O:4][C@@H:5]1[C@@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:17]([O:23][C@H:24]2[O:41][C@H:40]([CH2:42][O:43][C:44](=[O:46])[CH3:45])[C@@H:35]([O:36][C:37](=[O:39])[CH3:38])[C@H:30]([O:31][C:32](=[O:34])[CH3:33])[C@H:25]2[O:26][C:27](=[O:29])[CH3:28])[C@@H:16]([CH2:47][O:48][C:49](=[O:51])[CH3:50])[O:15][C@H:6]1[S:7][C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=1)(=[O:3])[CH3:2].N1C=[CH:56][CH:55]=[CH:54][C:53]=1[CH2:58][C:59]#[N:60].[C:61](Cl)(=[O:71])[CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][C:68](Cl)=[O:69].[OH2:73]>C(#N)C>[C:1]([O:4][C@@H:5]1[C@@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:17]([O:23][C@H:24]2[O:41][C@H:40]([CH2:42][O:43][C:44](=[O:46])[CH3:45])[C@@H:35]([O:36][C:37](=[O:39])[CH3:38])[C@H:30]([O:31][C:32](=[O:34])[CH3:33])[C@H:25]2[O:26][C:27](=[O:29])[CH3:28])[C@@H:16]([CH2:47][O:48][C:49](=[O:51])[CH3:50])[O:15][C@H:6]1[S:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:61](=[O:71])[CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][C:68]([NH:60][C:59]2[CH:58]=[CH:53][C:54]([S:7][C@@H:6]3[O:15][C@H:16]([CH2:47][O:48][C:49](=[O:51])[CH3:50])[C@@H:17]([O:23][C@H:24]4[O:41][C@H:40]([CH2:42][O:43][C:44](=[O:46])[CH3:45])[C@@H:35]([O:36][C:37](=[O:39])[CH3:38])[C@H:30]([O:31][C:32](=[O:34])[CH3:33])[C@H:25]4[O:26][C:27](=[O:29])[CH3:28])[C@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:5]3[O:73][C:1](=[O:3])[CH3:2])=[CH:55][CH:56]=2)=[O:69])=[CH:10][CH:9]=1)(=[O:3])[CH3:2]

参加物

6

反応物 4

HCID 962WaterHCID 75959Pyridine-2-acetonitrileHCID 534653Octanedioyl dichloride2 回HCID 132789934-aminophenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl)-1-thio-beta-D-glucopyranoside

生成物 1

HCID 53876502N,N'-Bis[4-[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl)-beta-D-glucopyranosylthio]phenyl]octanediamide

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a stirred solution of 25 g of 4-aminophenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside in 250 ml of a dry mixture of pyridine-acetonitrile (1:1) was added a solution of 3.55 g of suberoyl chloride in 10 ml of acetonitrile. This mixture was allowed to stand, under argon, for 18 hours. An additional 0.2 ml of suberoyl chloride was added, the solution was allowed to stand for an additional 18 hours and was then poured into 2 liters of water. After stirring for 15 minutes, the oil was separated and extracted into 500 ml of dichloromethane. The extract was washed twice with 500 ml portions of 0.5 N hydrochloric acid, then with saturated aqueous sodium chloride solution, dried and taken to dryness, giving 28 g of the desired product as a white foam.

後処理

  1. waitto stand for an additional 18 hours
  2. customthe oil was separated
  3. extractionextracted into 500 ml of dichloromethane
  4. washThe extract was washed twice with 500 ml portions of 0.5 N hydrochloric acid
  5. dry with materialwith saturated aqueous sodium chloride solution, dried

出典と根拠

ORDレコード
ord-999076dc251947d38a5b74f7534bf352
出典データセット
uspto-grants-1983_08
特許番号
US04399126

関連ノート

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