Bromine → HCID 11463747, compound

HRID 1821063Notes

Reaction equation

HRID 1821063 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:17]([O:18][C:19](=[O:21])[CH3:20])[C@H:16]([CH3:22])[O:15][C@@H:7](SC2C=CC=CC=2)[C@@H:6]1[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=[O:3])[CH3:2].[Br:31]Br>C(Cl)Cl>[C:1]([O:4][C@@H:5]1[C@@H:17]([O:18][C:19](=[O:21])[CH3:20])[C@H:16]([CH3:22])[O:15][C@@H:7]([Br:31])[C@@H:6]1[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24408BromineHCID 46782732Phenyl 3,4-di-O-acetyl-2-O-benzyl-6-deoxy-1-thio-alpha-L-mannopyranoside

Product 1

HCID 11463747HCID 11463747, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution containing 1.00 g (2.32 mmol) of 8 in 25 mL of anhydrous CH2Cl2 at 0° C. under argon was added 0.50 g (0.16 mL, 3.14 mmol) of Br2. The reaction mixture was stirred at 0° C. for 1 h. The reaction mixture was diluted with 20 mL of CH2Cl2 and washed with 100 mL of 3% aq NaHSO3. The organic layer was separated, dried (MgSO4) and concentrated under diminished pressure. The residue was then purified by flash chromatography on a silica gel column (26×4 cm).

Workup

  1. washwashed with 100 mL of 3% aq NaHSO3
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under diminished pressure
  5. customThe residue was then purified by flash chromatography on a silica gel column (26×4 cm)

Sources & evidence

ORD record
ord-cba4be8a96eb429f865275fa42852db2
Source dataset
uspto-grants-2009_10
Patent number
US07605241B2

Reaction notes

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