Hydrogen Bromide → alpha-D-Glucopyranosyl bromide, tetraacetate

HRID 1900241Notes

Reaction equation

HRID 1900241 reaction equation
[C:1]([O:4][C@H:5]([C@H:8]([C@@H:13]([C@@H:18]([CH2:23][O:24][C:25](=[O:27])[CH3:26])[O:19][C:20](=O)C)[O:14][C:15](=[O:17])[CH3:16])[O:9][C:10](=[O:12])[CH3:11])C=O)(=[O:3])[CH3:2].[BrH:28]>C(O)(=O)C>[CH3:26][C:25]([O:24][CH2:23][C@H:18]1[O:19][C@H:20]([Br:28])[C@H:5]([O:4][C:1]([CH3:2])=[O:3])[C@@H:8]([O:9][C:10]([CH3:11])=[O:12])[C@@H:13]1[O:14][C:15]([CH3:16])=[O:17])=[O:27]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 92972D-Glucose, 2,3,4,5,6-pentaacetate

Product 1

HCID 101776alpha-D-Glucopyranosyl bromide, tetraacetateYield 74%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

First, 14 g of glucose pentaacetate, from Sigma Chemical Company, was dissolved in 60 ml of 30% HBr in acetic acid and allowed to stand a 4° C. for 69 hours. The acetic acid was removed. The residue was dissolved in 100 ml of chloroform, washed twice with 100 ml of saturated NaHCO3, dried over MgSO4, concentrated, and crystallized from 95% ethanol to give 10.88 g (74%) of acetobromoglucose.

Workup

  1. customThe acetic acid was removed
  2. dissolutionThe residue was dissolved in 100 ml of chloroform
  3. washwashed twice with 100 ml of saturated NaHCO3
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customcrystallized from 95% ethanol

Sources & evidence

ORD record
ord-59599ef11fe84f089518bfad4dbc1789
Source dataset
uspto-grants-1996_11
Patent number
US05574177

Reaction notes

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