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

반응식

HRID 434740 반응식
[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]

참가 물질

6

반응물 4

HCID 962WaterHCID 75959Pyridine-2-acetonitrileHCID 534653Octanedioyl dichloride2회HCID 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

생성물 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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-999076dc251947d38a5b74f7534bf352
출처 데이터셋
uspto-grants-1983_08
특허 번호
US04399126

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