Hydrogen Bromide → alpha-D-Glucopyranosyl bromide, tetraacetate

HRID 2252449Notes

Reaction equation

HRID 2252449 reaction equation
C(O[C@H:5]1[O:22][C@H:21]([CH2:23][O:24][C:25](=[O:27])[CH3:26])[C@@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:6]1[O:7][C:8](=[O:10])[CH3:9])(=O)C.[BrH:28].C(OCC)(=O)C.CCCCCC>ClCCl>[C:8]([O:7][C@@H:6]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@@H:21]([CH2:23][O:24][C:25](=[O:27])[CH3:26])[O:22][C@@H:5]1[Br:28])(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 2723636alpha-D-Glucopyranosyl pentaacetateHCID 21226206Ethyl acetate hexane

Product 1

HCID 101776alpha-D-Glucopyranosyl bromide, tetraacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,2,3,4,6-penta-O-acetyl-α-D-glucopyranose (1.0 g, 2.60 mmol) was dissolved in 20 mL of dichloromethane and 1.90 mL of hydrobromic acid (33% in acetic acid) at 0° C., and the reaction was stirred while warming to room temperature. TLC (40% ethyl acetate-hexane) after 18 h showed complete consumption of the starting material and formation of a higher running spot. The reaction was slowly diluted with saturated sodium bicarbonate (25 mL), extracted into dichloromethane (2×100 mL), dried over sodium sulfate, filtered and concentrated to afford 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide which was used without purification.

Workup

  1. customconsumption of the starting material and formation of
  2. additionThe reaction was slowly diluted with saturated sodium bicarbonate (25 mL)
  3. extractionextracted into dichloromethane (2×100 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e27d81aea01b42cba5cb075ac8bd9ad7
Source dataset
uspto-grants-2008_01
Patent number
US07320972B2

Reaction notes

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