Hydrogen Bromide → 1,2,4,6-tetra-O-acetyl-3-O-benzyl-beta-D-glucopyranose

HRID 1746240Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1746240
Br.[C:2]([O:5][C@H:6]1[O:27][C@H:26]([CH2:28][O:29][C:30](=[O:32])[CH3:31])[C@@H:21]([O:22][C:23](=[O:25])[CH3:24])[C@H:12]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C@H:7]1[O:8][C:9](=[O:11])[CH3:10])(=[O:4])[CH3:3]>C(O)(=O)C>[C:2]([O:5][C@@H:6]1[O:27][C@H:26]([CH2:28][O:29][C:30](=[O:32])[CH3:31])[C@@H:21]([O:22][C:23](=[O:25])[CH3:24])[C@H:12]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C@H:7]1[O:8][C:9](=[O:11])[CH3:10])(=[O:4])[CH3:3]

Komponenten

4

Edukt 2

HCID 260Hydrogen BromideHCID 21637718HCID 21637718, Verbindung

Produkt 1

HCID 111129491,2,4,6-tetra-O-acetyl-3-O-benzyl-beta-D-glucopyranoseAusbeute 101,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Hydrogen bromide (33% solution in acetic acid) (100 mL) was slowly added to the 69 g of 1,2,4,6-tetra-O-acetyl-3-O-benzyl-α-D-glucopyranose from Step 4 and cooled to 0° C. to produce a solution of 1,2,4,6-tetra-O-acetyl-3-O-benzyl-β-D-glucopyranose (70 g) in acetic acid (140 mL). The mixture was stirred at 0° C. for 1 hour and then diluted with chloroform (1 L). Next, the reaction mixture was washed with water and saturated sodium bicarbonate and then dried over sodium sulfate. The drying agent and solvent were removed to obtain crude 2,4,6-tri-O-acetyl-3-O-benzyl-α-D-glucosyl bromide. The product was used in the next step without further purification. Additional information about this step appears in Journal of Organic Chemistry, 1962, 3089-3092. The entire article is incorporated herein by reference.

Quellen und Nachweise

ORD-Eintrag
ord-857144665ef349fa85ee0d14cacc6425
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09149489B2

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