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

HRID 1746240Notes

Reaction equation

HRID 1746240 reaction equation
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]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 21637718HCID 21637718, compound

Product 1

HCID 111129491,2,4,6-tetra-O-acetyl-3-O-benzyl-beta-D-glucopyranoseYield 101.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

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.

Sources & evidence

ORD record
ord-857144665ef349fa85ee0d14cacc6425
Source dataset
uspto-grants-2015_10
Patent number
US09149489B2

Reaction notes

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