Stannous Chloride → 1-Thiophenyl-(2,3,4-tri-O-acetyl-6-O-benzyl-beta-D-galactopyranosyl)-(1-4)-[(2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl)-(1-3)]-2-deoxy-2-acetamido-beta-D-glucopyranose

HRID 130006

Reaktionsgleichung

Reaktionsgleichung von HRID 130006
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C@:6]1([O:41][C@H:40]([CH2:42][OH:43])[C@@H:11]([O:12][C@@H:13]2[O:30][C@H:29]([CH2:31][O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C@H:24]([O:25][C:26](=[O:28])[CH3:27])[C@H:19]([O:20][C:21](=[O:23])[CH3:22])[C@H:14]2[O:15][C:16](=[O:18])[CH3:17])[C@H:9]([OH:10])[C@H:8]1[NH:44][C:45](=[O:47])[CH3:46])[OH:7].S1C=CC=C1[C@@:53]1([O:83][C@@H:82]([CH3:84])[C@@H:73]([O:74][CH2:75][C:76]2[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=2)[C@@H:64]([O:65][CH2:66][C:67]2[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=2)[C@@H:55]1[O:56][CH2:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)O.[Sn](Cl)Cl>C(OCC)C.Cl([O-])(=O)(=O)=O.[Ag+]>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C@:6]1([O:41][C@H:40]([CH2:42][OH:43])[C@@H:11]([O:12][C@@H:13]2[O:30][C@H:29]([CH2:31][O:32][CH2:33][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[C@H:24]([O:25][C:26](=[O:28])[CH3:27])[C@H:19]([O:20][C:21](=[O:23])[CH3:22])[C@H:14]2[O:15][C:16](=[O:18])[CH3:17])[C@H:9]([OH:10])[C@@:8]1([C@@H:53]1[O:83][C@@H:82]([CH3:84])[C@@H:73]([O:74][CH2:75][C:76]2[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=2)[C@@H:64]([O:65][CH2:66][C:67]2[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=2)[C@@H:55]1[O:56][CH2:57][C:58]1[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=1)[NH:44][C:45](=[O:47])[CH3:46])[OH:7]

Komponenten

6

Edukt 3

HCID 24479Stannous ChlorideHCID 867491301-Thiophenyl-(2,3,4-tri-O-acetyl-6-O-benzyl-beta-D-galactopyranosyl)-(1-4)-2-deoxy-2-acetamido-beta-D-glucopyranoseHCID 867491321-Thiophenyl-2,3,4-tri-O-benzyl-beta-L-fucose

Produkt 1

HCID 1317192141-Thiophenyl-(2,3,4-tri-O-acetyl-6-O-benzyl-beta-D-galactopyranosyl)-(1-4)-[(2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl)-(1-3)]-2-deoxy-2-acetamido-beta-D-glucopyranose

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24562Silver perchlorateKatalysatorHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Compound [13] (0.2-4.81 g, 0.234-5.78 mmol) is dissolved with compound [17] (0.17-4.15 g, 0.37-9.25 mmol) in dry diethyl ether (5-100 ml) and stirred with 4 Å molecular sieves (0.1-6.8 g), silver perchlorate (0.15-3.59 g 0.702-17.34 mmol) and tin(II) chloride (0.13-3.29 g, 0.702-17.34 mmol) until the reaction is complete. The mixture is subsequently filtered, and the crude product compound [18] obtained after concentration is purified by chromatography on silica gel with an ethyl acetate/isohexane gradient (0.25-6.2 g, 0.2-4.91 mmol, about 85% yield). FAB-MS: M+H+ =1262. NMR data consistent with Nicolaou et al., J. Am. Chem. Soc. 114:3127 (1992) and C. W. Hummel, Ph.D. Dissertation, University of California, San Diego (1993).

Aufarbeitung

  1. filtrationThe mixture is subsequently filtered

Quellen und Nachweise

ORD-Eintrag
ord-9b0bf76d94ff4ef8a4165deb1aee630b
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05470843

Verknüpfte Notizen

Wird geladen…