Triethylamine → Oleyl 2,3,4-tri-O-acetyl-1-thio-beta-L-fucopyranoside

HRID 128201Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 128201
[C:1]([O:4][C@H:5]1[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@H:9]([CH3:20])[O:8][C@@H:6]1[SH:7])(=[O:3])[CH3:2].[CH2:21](I)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]/[CH:29]=[CH:30]\[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38].C(N(CC)CC)C>ClCCl>[C:1]([O:4][C@H:5]1[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@H:9]([CH3:20])[O:8][C@@H:6]1[S:7][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]/[CH:29]=[CH:30]\[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 10894154Oleyl iodideHCID 232389082,3,4-tri-O-acetyl-1-thio-beta-L-fucopyranose

Produkt 1

HCID 70572110Oleyl 2,3,4-tri-O-acetyl-1-thio-beta-L-fucopyranoside

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranose (2.0 g, 6.5 mmol) and oleyl iodide (2.5 g, 6.6 mmol) in dichloromethane (40 ml) containing triethylamine (1 ml) is kept under nitrogen for 2 days at room temperature. The solution is worked up in the normal manner and the resulting syrup is column chromatographed on silica gel with 2-10% ethyl acetate in chloroform as eluents. Oleyl 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranoside is isolated as a syrup (1.2 g, 32%), [α]D +26° (c, 2.19, chloroform).

Aufarbeitung

  1. customchromatographed on silica gel with 2-10% ethyl acetate in chloroform as eluents

Quellen und Nachweise

ORD-Eintrag
ord-7f9fa20bbbb14e818172124164ac4b40
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04259324

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