Methanol → Benzyl 6-bromo-2,6-dideoxy-beta-D-glucopyranoside

HRID 276097

Reaktionsgleichung

Reaktionsgleichung von HRID 276097
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:20]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C@@H:21]1[O:28][C@H:27]([CH2:29]O)[C@@H:25]([OH:26])[C@H:23]([OH:24])[CH2:22]1.C(Br)(Br)(Br)[Br:39].CO>N1C=CC=CC=1>[Br:39][CH2:29][C@H:27]1[O:28][C@@H:21]([O:20][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:22][C@@H:23]([OH:24])[C@@H:25]1[OH:26]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 53805352Benzyl 2-deoxy-beta-D-glucopyranoside

Produkt 1

HCID 70168265Benzyl 6-bromo-2,6-dideoxy-beta-D-glucopyranosideAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A solution of triphenylphosphine (4.5 g, 17.3 mmol, 2.2 eq) in pyridine (30 mL) was added dropwise to a cooled solution of Compound 1 (2.0 g, 7.9 mmol) and CBr4 (3.1 g, 9.4 mmol) in pyridine (30 mL) at zero degrees C. The mixture was then heated at 50° C. for 10 hours. After cooling, methanol (5 mL) was added dropwise, and the mixture was concentrated. The product was purified by flash column chromatography with CHCl3—MeOH (32:1) to give 1.82 g (yield 73 percent) of Compound 2.

Aufarbeitung

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated
  3. customThe product was purified by flash column chromatography with CHCl3—MeOH (32:1)

Quellen und Nachweise

ORD-Eintrag
ord-7c0b30cd64184805a2bbd601e8d0421f
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06353095B1

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