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

https://huagongshe.com/de/reaction/653347

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	Sodium	HCID 5360545	—
Edukt	2-(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-glucopyranoside	HCID 18608304	—
Edukt	Chloroform methanol water	HCID 21866399	—
Lösungsmittel	Methanol	HCID 887	—
Produkt	Carbomethoxyethylthioethyl 4-O-(4-O-[6-O-{A-D-glucopyranosyl}-A-D-glucopyranosyl]-A-D-glucopyranosyl)-B-D-glucopyranoside	HCID 54077541	84%

Reaktionsschritte

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.

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US04675392
Quelldatensatz	uspto-grants-1987_06
ORD ID	ord-c3576d8cd232457d8ae2283a16f2c96b
Quellennotiz	uspto-grants-1987_06