Sodium → Carbomethoxyethylthioethyl 4-O-(4-O-[6-O-{A-D-glucopyranosyl}-A-D-glucopyranosyl]-A-D-glucopyranosyl)-B-D-glucopyranoside

HRID 653347

Reaktionsgleichung

Reaktionsgleichung von HRID 653347
C([O:4][C@@H:5]1[C@@H:20]([O:21]C(=O)C)[C@H:19]([O:25][C@H:26]2[O:83][C@H:82]([CH2:84][O:85]C(=O)C)[C@@H:37]([O:38][C@H:39]3[O:56][C@H:55]([CH2:57][O:58][C@H:59]4[O:76][C@H:75]([CH2:77][O:78]C(=O)C)[C@@H:70]([O:71]C(=O)C)[C@H:65]([O:66]C(=O)C)[C@H:60]4[O:61]C(=O)C)[C@@H:50]([O:51]C(=O)C)[C@H:45]([O:46]C(=O)C)[C@H:40]3[O:41]C(=O)C)[C@H:32]([O:33]C(=O)C)[C@H:27]2[O:28]C(=O)C)[C@@H:18]([CH2:89][O:90]C(=O)C)[O:17][C@H:6]1[O:7][CH2:8][CH2:9][S:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])(=O)C.[Na].C(Cl)(Cl)Cl.CO.O>CO>[C@H:59]1([O:58][CH2:57][C@H:55]2[O:56][C@H:39]([O:38][C@@H:37]3[C@@H:82]([CH2:84][OH:85])[O:83][C@H:26]([O:25][C@@H:19]4[C@@H:18]([CH2:89][OH:90])[O:17][C@@H:6]([O:7][CH2:8][CH2:9][S:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[C@H:5]([OH:4])[C@H:20]4[OH:21])[C@H:27]([OH:28])[C@H:32]3[OH:33])[C@H:40]([OH:41])[C@@H:45]([OH:46])[C@@H:50]2[OH:51])[O:76][C@H:75]([CH2:77][OH:78])[C@@H:70]([OH:71])[C@H:65]([OH:66])[C@H:60]1[OH:61]

Komponenten

5

Edukt 3

HCID 5360545SodiumHCID 186083042-(2-Methoxycarbonylethylthio)ethyl 2,3,6-tri-O-acetyl-4-O-{2,3,6-tri-O-acetyl-4-O-[2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl)-alpha-D-glucopyranosyl]-alpha-D-glucopyranosyl}-beta-D-glucopyranosideHCID 21866399Chloroform methanol water

Produkt 1

HCID 54077541Carbomethoxyethylthioethyl 4-O-(4-O-[6-O-{A-D-glucopyranosyl}-A-D-glucopyranosyl]-A-D-glucopyranosyl)-B-D-glucopyranosideAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

Compound 94 (3.0 g, 2.2 mmol) was dissolved in methanol (25 ml) and added to a solution of sodium (1 mg) in methanol (75 ml). The reaction mixture was monitored by TLC (chloroform:methanol:water 65:35:10, lower phase). After 9 h at room temperature and 30 min at 40°, the solvent was removed and the residue was chromatographed (SiO2, chloroform:methanol:water, 65:35:10, lower phase) to give 98 (1.50 g, 84%). [α]D25 +113° (c 0.7, water). 1H-NMR (D2O, TSP) δ 5.41 (d, 2H, J=3.5 Hz, H1' and H1"), 4.98 (d, 1H, J=3.6 Hz, H1"'), 4.53 (d, 1H, J=7.9 Hz, H1), 3.75 (s, 3H, MeO). 13C-NMR (D2O, TSP) δ 177.4 (CO), 104.3 (Cl), 102.0, 101.6, 100.2 (Cl', Cl", Cl"'), 79.3, 79.1, 78.3, 76.7, 75.4, 75.2, 75.1, 73.9, 73.8, 73.6, 73.5, 73.3,,71.6, 71.5, 71.1, 68.0, 62.8, 62.7, 62.6, 62.6, 54.5, 36.3, 32.9, 28.6.

Aufarbeitung

  1. custom30 min at 40°, the solvent was removed
  2. customthe residue was chromatographed (SiO2, chloroform:methanol:water, 65:35:10, lower phase)

Quellen und Nachweise

ORD-Eintrag
ord-c3576d8cd232457d8ae2283a16f2c96b
Quelldatensatz
uspto-grants-1987_06
Patentnummer
US04675392

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