Hydrogen Bromide → HCID 131716981, compound

HRID 1030780Notes

Reaction equation

HRID 1030780 reaction equation
[BrH:1].[C:2]([O:5][CH2:6][C:7]1([CH2:29][O:30][C:31](=[O:33])[CH3:32])[O:16][CH:11](OC(=O)C)[C@H:10]([O:17][C:18](=[O:20])[CH3:19])[C@@H:9]([O:21][C:22](=[O:24])[CH3:23])[C@H:8]1[O:25][C:26](=[O:28])[CH3:27])(=[O:4])[CH3:3]>C(O)(=O)C>[C:2]([O:5][CH2:6][C:7]1([CH2:29][O:30][C:31](=[O:33])[CH3:32])[O:16][C@@H:11]([Br:1])[C@H:10]([O:17][C:18](=[O:20])[CH3:19])[C@@H:9]([O:21][C:22](=[O:24])[CH3:23])[C@H:8]1[O:25][C:26](=[O:28])[CH3:27])(=[O:4])[CH3:3]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 15041765HCID 15041765, compound

Product 1

HCID 131716981HCID 131716981, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Glacial acetic acid (60 ml) is saturated with dry gaseous HBr for 30 minutes at 18°-20° C. This solution is mixed with 5-C-acetoxymethyl-1,2,3,4,6-penta-O-acetyl-L-arabino-hexopyranose (7) (6.0 g, 0.013 ml) and is stirred at an ambient temperature for 3.5 hours. Workup of the reaction mixture involves: dilution with methylene chloride (150 ml), washing with ice-water, sat. sodium bicarbonate solution, and water again. After drying the methylene chloride solution with sodium sulfate (anhydrous), evaporation of the solvent produces crude 5-C-acetoxymethyl-2,3,4,6-tetra-O-acetyl-α-L-arabino-hexopyranosyl bromide (18) (3 g) which is dried under high vacuum for 30 minutes and is used for the glycosidation reactions without further purification.

Workup

  1. washdilution with methylene chloride (150 ml), washing with ice-water, sat. sodium bicarbonate solution, and water again
  2. dry with materialAfter drying the methylene chloride solution
  3. customwith sodium sulfate (anhydrous), evaporation of the solvent

Sources & evidence

ORD record
ord-54f8eb254b844ddba254c6ab8298dece
Source dataset
uspto-grants-1992_04
Patent number
US05106967

Reaction notes

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