Hydrogen Bromide → 2,3,4-Tri-O-Acetyl-6-Deoxy-alpha-D-Glucopyranosyl Bromide

HRID 430448

Reaktionsgleichung

Reaktionsgleichung von HRID 430448
O=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH3:11])[OH:10])[OH:8])[OH:6])[OH:4].[BrH:12]>C(O)(=O)C.ClCCl>[C:3]([O:10][C@@H:9]1[C@@H:7]([O:8][C:5](=[O:6])[CH3:7])[C@H:5]([O:6][C:9](=[O:10])[CH3:11])[C@@H:3]([CH3:2])[O:4][C@@H:11]1[Br:12])(=[O:4])[CH3:2]

Komponenten

5

Edukt 2

HCID 260Hydrogen BromideHCID 935796-Deoxyglucose

Produkt 1

HCID 128982142,3,4-Tri-O-Acetyl-6-Deoxy-alpha-D-Glucopyranosyl BromideAusbeute 85,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittel2×HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

In a 10 mL round bottom flask containing 10 mL of glacial acetic acid was placed 6-deoxyglucose (332.3 mg) and the reaction was cooled to 0° C. Hydrobromic acid in glacial acetic acid (5 mL of a 30 wt. % solution) was added dropwise. The reaction was stirred for 4 hours. The reaction was diluted with 100 mL of dichloromethane and washed with 50 mL ice water and then 50 mL of cold saturated aqueous sodium bicarbonate. The organic layer was dried over magnesium sulfate and filtered. The solvent was removed in vacuo to yield the title compound as a yellow solid (636.5 mg, 85.4%) and the product was used without further purification as in Example 1. MS (FAB) calculated for C12H17O7Br (M−Br) 273.1, found 273.1.

Aufarbeitung

  1. washwashed with 50 mL ice water
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customThe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-882058027a21424792d6d3b0e08f63d0
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06323176B1

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