Hydrogen Bromide → HCID 131716981, compound

HRID 973528Notes

Reaction equation

HRID 973528 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, 0.013ml) 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-5b7c097b859d4b248a4ef814f4577955
Source dataset
uspto-grants-1991_11
Patent number
US05064672

Reaction notes

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