Hydrogen Bromide → HCID 12905063, compound

HRID 1795719Notes

Reaction equation

HRID 1795719 reaction equation
C(O[CH:5]1[O:34][C@H:33]([CH2:35][O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C@H:24]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C@H:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@H:6]1[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=O)C.[BrH:44].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.C(OC(C)C)(C)C>[CH2:8]([O:7][C@@H:6]1[C@@H:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@@H:24]([O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C@@H:33]([CH2:35][O:36][CH2:37][C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[O:34][C@@H:5]1[Br:44])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 260Hydrogen Bromide2×HCID 516892Sodium BicarbonateHCID 1130776780300-97-6

Product 1

HCID 12905063HCID 12905063, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 7914Diisopropyl EtherSolvent2×

Conditions

Temperature
-5 °C

Procedure

2,3,4,6-Tetra-O-benzyl-D-galactopyranosyl acetate (79.8 g) was dissolved in a mixed solution of toluene (160 mL) and isopropyl ether (520 mL) and then cooled to −10-0° C. To the solution was added a solution containing 2.0 equivalent amount of HBr in isopropyl ether (2.8 mmol/mL, about 100 mL). After the reaction solution was stirred at −10-0° C. for about 90 minutes, a 5% aqueous solution of sodium hydrogencarbonate was poured thereto and stirred to neutralize the excess HBr. The whole of the solution was transferred to a separatory funnel to cause separation into an aqueous layer and an organic layer. The aqueous layer obtained was discarded and the organic layer was washed with a 10% aqueous solution of sodium chloride twice. The organic layer was concentrated under reduced pressure, thereby giving a syrup product of 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl bromide (Gal-Br).

Workup

  1. additionTo the solution was added a solution
  2. stirringstirred
  3. customThe whole of the solution was transferred to a separatory funnel
  4. customseparation into an aqueous layer
  5. customThe aqueous layer obtained
  6. washthe organic layer was washed with a 10% aqueous solution of sodium chloride twice
  7. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-de4ec67deb4c4c4cb584577ee94bad35
Source dataset
uspto-grants-2006_04
Patent number
US07029671B1

Reaction notes

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