Triethylamine → 2-(1-adamantyl)ethyl 2,3,4-tri-O-acetyl-1-thio-beta-L-fucopyranoside

HRID 128197

Reaktionsgleichung

Reaktionsgleichung von HRID 128197
[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].[C:21]12([CH2:31][CH2:32]I)[CH2:30][CH:25]3[CH2:26][CH:27]([CH2:29][CH:23]([CH2:24]3)[CH2:22]1)[CH2:28]2.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][CH2:32][CH2:31][C:21]12[CH2:30][CH:25]3[CH2:26][CH:27]([CH2:29][CH:23]([CH2:24]3)[CH2:22]1)[CH2:28]2)(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 221412941-(2-Iodoethyl)adamantaneHCID 232389082,3,4-tri-O-acetyl-1-thio-beta-L-fucopyranose

Produkt 1

HCID 228151692-(1-adamantyl)ethyl 2,3,4-tri-O-acetyl-1-thio-beta-L-fucopyranosideAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranose (2.14 g, 7 mmol) and 2-(1-adamantyl)ethyl iodide (2.03 g, 7 mmol) in dichloromethane (40 ml) containing triethylamine (0.71 g) is kept under nitrogen for 3 days. The reaction mixture is washed successively with N hydrochloric acid, aqueous sodium bicarbonate and water. The dried solution is concentrated to a residue which is taken up in ethanol to remove crystals (0.3 g, 2-(1-adamantyl)ethyl iodide). The mother liquor is put on a silica gel column and eluted with 1% methanol in chloroform. The desired fractions are pooled and evaporated to give 2-(1-adamantyl)ethyl 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranoside (1.8 g, 66%), [α]D +18° (c, 1.5, chloroform). Deblocking of this material with sodium methoxide in methanol affords the title compound, m.p. 130°-131°, [α]D +31° (c, 1.07, chloroform).

Aufarbeitung

  1. washThe reaction mixture is washed successively with N hydrochloric acid, aqueous sodium bicarbonate and water
  2. concentrationThe dried solution is concentrated to a residue which
  3. customto remove crystals (0.3 g, 2-(1-adamantyl)ethyl iodide)
  4. washeluted with 1% methanol in chloroform
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-beed8087c521461094e68311c293a07e
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04259324

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