Triethylamine → HCID 131723194, Verbindung

HRID 843211Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 843211
[CH3:1][C@@H:2]([OH:12])[C@@H:3]([OH:11])[C@H:4]([O:9][CH3:10])[C@@H:5]([OH:8])[CH:6]=[O:7].[CH3:13][C@H:14]1[O:19][C@@H:18]([OH:20])[CH2:17][C@H:16]([O:21][CH3:22])[C@@H:15]1[OH:23].[Sn](Cl)Cl.C(N(CC)CC)C>ClCCl.FC(F)(F)S([O-])(=O)=O.[Ag+]>[CH3:1][C@@H:2]([OH:12])[C@@H:3]([OH:11])[C@H:4]([O:9][CH3:10])[C@@H:5]([OH:8])[CH:6]=[O:7].[CH3:13][C@H:14]1[O:19][C@@H:18]([OH:20])[CH2:17][C@H:16]([O:21][CH3:22])[C@@H:15]1[OH:23]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 24479Stannous ChlorideHCID 193394AcofrioseHCID 4414172,6-Dideoxy-3-O-methylhexopyranose

Produkt 1

HCID 131723194HCID 131723194, VerbindungAusbeute 15 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 76223Silver(I) trifluoromethanesulfonateKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

A solution of thevetose (50 A) (1,5 g), cymarose (40) (1,3 g), and molecular sieves 4 Å in dichloromethane is stirred at room temperature for 1 hour. The reaction mixture is cooled to −15° C., and tin (II) chloride (0,8 g) and silver trifluoromethanesulphonate (1,1 g) are added. The mixture is stirred at −15° C. for 16 hours, after which triethylamine (0,5 ml) is added. The reaction product is filtered and the dichloromethane is evaporated. The dissaccharide (53) is purified by silica gel column chromatography eluting with ethyl acetate:hexane (2:8), yield 15%.

Aufarbeitung

  1. filtrationThe reaction product is filtered
  2. customthe dichloromethane is evaporated
  3. customThe dissaccharide (53) is purified by silica gel column chromatography
  4. washeluting with ethyl acetate:hexane (2:8), yield 15%

Quellen und Nachweise

ORD-Eintrag
ord-60f0ea786d13431096096d5ab4ac2b4c
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06376657B1

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