methyl alpha-D-glucopyranoside → HCID 22819440, Verbindung

HRID 1447499Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1447499
[CH3:1][C:2]1([CH3:26])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6](/[C:14](/[CH3:25])=[CH:15]/[C:16]3[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=3)[CH:5]=[CH:4][C:3]1=2.[O:27]([CH3:39])[C@H:28]1[O:36][C@H:35]([CH2:37][OH:38])[C@@H:33]([OH:34])[C@H:31]([OH:32])[C@H:29]1[OH:30]>CCOCC.N1C=CC=CC=1>[CH3:1][C:2]1([CH3:26])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6](/[C:14](/[CH3:25])=[CH:15]/[C:16]3[CH:24]=[CH:23][C:19]([C:20]([O:30][C@@H:29]4[C@@H:31]([OH:32])[C@H:33]([OH:34])[C@@H:35]([CH2:37][O:38][C:20](=[O:21])[C:19]5[CH:23]=[CH:24][C:16](/[CH:15]=[C:14](/[C:6]6[CH:5]=[CH:4][C:3]7[C:2]([CH3:26])([CH3:1])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]=7[CH:7]=6)\[CH3:25])=[CH:17][CH:18]=5)[O:36][C@@H:28]4[O:27][CH3:39])=[O:21])=[CH:18][CH:17]=3)[CH:5]=[CH:4][C:3]1=2.[CH3:1][C:2]1([CH3:26])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6](/[C:14](/[CH3:25])=[CH:15]/[C:16]3[CH:24]=[CH:23][C:19]([C:20]([O:32][C@H:31]4[C@H:33]([OH:34])[C@@H:35]([CH2:37][O:38][C:20](=[O:21])[C:19]5[CH:23]=[CH:24][C:16](/[CH:15]=[C:14](/[C:6]6[CH:5]=[CH:4][C:3]7[C:2]([CH3:26])([CH3:1])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]=7[CH:7]=6)\[CH3:25])=[CH:17][CH:18]=5)[O:36][C@H:28]([O:27][CH3:39])[C@@H:29]4[OH:30])=[O:21])=[CH:18][CH:17]=3)[CH:5]=[CH:4][C:3]1=2

Komponenten

6

Edukt 2

HCID 64947methyl alpha-D-glucopyranosideHCID 12836534HCID 12836534, Verbindung

Produkt 2

HCID 22819440HCID 22819440, VerbindungHCID 70523303methyl 2,6-bis-O-[p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-propenyl]-benzoyl]-alpha-D-glucopyranoside

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 100 mmol of p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-propenyl]-benzoyl chloride in 450 ml of ether was added while stirring at 0° C. over a period of 1 hour to a solution of 19.5 g of methyl α-D-glucopyranoside in 500 ml of pyridine. The mixture was stirred at 0° C. for a further 4 hours and at room temperature for 16 hours and then evaporated to dryness. The residue was dissolved in ethyl acetate and the extract was washed with 3 N hydrochloric acid, water, saturated aqueous sodium bicarbonate solution and water. After drying over sodium sulphate, the organic phase was evaporated and the residue was chromatographed on silica gel (hexane/ethyl acetate) to give methyl 2,6-bis-O-[p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-propenyl]-benzoyl]-α-D-glucopyranoside, melting point 203°-204° C. (from ethyl acetate), [α]D25 =+27.4° (c=1 in chloroform), and methyl 3,6-bis-O-[p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-propenyl]-benzoyl]-α-D-glucopyranoside, melting point 128°-129° C. (with decomposition, from methanol), [α]D25 =+135° (c=1 in chloroform).

Aufarbeitung

  1. customevaporated to dryness
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washthe extract was washed with 3 N hydrochloric acid, water, saturated aqueous sodium bicarbonate solution and water
  4. dry with materialAfter drying over sodium sulphate
  5. customthe organic phase was evaporated
  6. customthe residue was chromatographed on silica gel (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-790f5b17a8354b518b477bd53a9b33d1
Quelldatensatz
uspto-grants-1982_02
Patentnummer
US04316983

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