Water → N,N',N"-Tris[4-[[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl)-beta-D-glucopyranosyl]thio]phenyl]-1,3,5-benzenetricarboxamide

HRID 1903052Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1903052
[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].[C:52]1([C:64](Cl)=[O:65])[CH:57]=[C:56]([C:58](Cl)=[O:59])[CH:55]=[C:54]([C:61](Cl)=[O:62])[CH:53]=1.[OH2:67]>N1C=CC=CC=1CC#N>[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:64]([C:52]2[CH:57]=[C:56]([C:58]([NH:14][C:11]3[CH:10]=[CH:9][C:8]([S:7][C@@H:6]4[O:15][C@H:16]([CH2:47][O:48][C:49](=[O:51])[CH3:50])[C@@H:17]([O:23][C@H:24]5[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]5[O:26][C:27](=[O:29])[CH3:28])[C@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:5]4[O:67][C:1](=[O:3])[CH3:2])=[CH:13][CH:12]=3)=[O:59])[CH:55]=[C:54]([C:61]([NH:14][C:11]3[CH:12]=[CH:13][C:8]([S:7][C@@H:6]4[O:15][C@H:16]([CH2:47][O:48][C:49](=[O:51])[CH3:50])[C@@H:17]([O:23][C@H:24]5[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]5[O:26][C:27](=[O:29])[CH3:28])[C@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:5]4[O:4][C:1](=[O:3])[CH3:2])=[CH:9][CH:10]=3)=[O:62])[CH:53]=2)=[O:65])=[CH:10][CH:9]=1)(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 962WaterHCID 78138Trimesoyl chlorideHCID 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

Produkt 1

HCID 53908218N,N',N"-Tris[4-[[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl)-beta-D-glucopyranosyl]thio]phenyl]-1,3,5-benzenetricarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 75959Pyridine-2-acetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 2.5 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 25 ml of pyridineacetonitrile (1:1) was added 300 mg of 1,3,5-benzenetricarboxylic acid chloride. The resulting solution was kept at ambient temperature, protected from moisture for 24 hours, then poured into 250 ml of water. The solution was extracted several times with chloroform. The combined extracts were washed with 0.5 N hydrochloric acid and saturated sodium chloride solution, dried with anhydrous magnesium sulfate and taken to dryness giving 2.7 g of the desired intermediate as a foam.

Aufarbeitung

  1. customwas kept at ambient temperature
  2. extractionThe solution was extracted several times with chloroform
  3. washThe combined extracts were washed with 0.5 N hydrochloric acid and saturated sodium chloride solution
  4. dry with materialdried with anhydrous magnesium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-6479fd670ee041bfa22d26e00c573857
Quelldatensatz
uspto-grants-1984_03
Patentnummer
US04435387

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