Hydrogen Bromide → HCID 10872911, compound

HRID 2107785Notes

Reaction equation

HRID 2107785 reaction equation
C(O[C@H:5]1[O:18][C@H:17]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[C@H:12]([O:13][C:14](=[O:16])[CH3:15])[C@H:7]([O:8][C:9](=[O:11])[CH3:10])[C@H:6]1[N:24]=[N+:25]=[N-:26])(=O)C.[BrH:27]>C(Cl)Cl.[Br-].C([N+](CC)(CC)CC)C>[C:9]([O:8][C@H:7]1[C@@H:12]([O:13][C:14](=[O:16])[CH3:15])[C@@H:17]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:18][C@H:5]([Br:27])[C@@H:6]1[N:24]=[N+:25]=[N-:26])(=[O:11])[CH3:10]

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 128212011,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranose

Product 1

HCID 10872911HCID 10872911, compound

Reagents, catalysts & solvents 2

HCID 6285Tetraethylammonium BromideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

1 ,3,4,6- Tetra-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranose (14) (500 mg) was dissolved in 50 mL CH2Cl2 (anhydrous), treated with 50 mL of CH2Cl2 saturated with HBr at 0° C., and stirred for two hours. Then 2 g of tetraethyl ammonium bromide was added and stirred overnight. Next, the solution was washed with 100 mL ice-cold water and concentrated. The residue was crystallized from ethyl ether and pentane to give 400 mg of 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl bromide (18).

Workup

  1. stirringstirred overnight
  2. washNext, the solution was washed with 100 mL ice-cold water
  3. concentrationconcentrated
  4. customThe residue was crystallized from ethyl ether and pentane

Sources & evidence

ORD record
ord-7dbba2ce2d814d939c3daf244fc584c4
Source dataset
uspto-grants-1990_06
Patent number
US04935503

Reaction notes

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