Pyridine → (2S,3R,4R,5S)-3,4,5-Tris(benzyloxy)-2-(benzyloxymethyl)-6-(3-(bromomethyl)-4-chlorophenyl)-tetrahydro-2H-pyran

HRID 46189Notes

Reaction equation

HRID 46189 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C@H:13]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C@@H:12]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C@H:11]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C@@H:10]([CH2:38][O:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[O:9]2)=[CH:4][C:3]=1[CH2:47]O.N1C=CC=CC=1.P(Br)(Br)[Br:56]>CCOCC.C(OCC)(=O)C>[CH2:31]([O:30][C@H:11]1[C@H:12]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C@@H:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([CH2:47][Br:56])[CH:4]=2)[O:9][C@H:10]1[CH2:38][O:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 24614Phosphorus tribromideHCID 67288226HCID 67288226, compound2×

Product 1

HCID 67287514(2S,3R,4R,5S)-3,4,5-Tris(benzyloxy)-2-(benzyloxymethyl)-6-(3-(bromomethyl)-4-chlorophenyl)-tetrahydro-2H-pyran

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2-chloro-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxy-methyl) tetrahydro-2H-pyran-2-yl)phenyl)methanol (compound 5, 130 g, 195 mmol) from Step 6 in ether (600 mL) at 0° C. was added pyridine (0.79 mL, 9.8 mmol) and phosphorus tribromide (6.4 mL, 68 mmol). The reaction was allowed to slowly warm to room temperature over 15 h and refluxed 1 h. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and washed with water then brine. The organic extract was dried over magnesium sulfate, filtered, and evaporated in vacuo to yield the title compound as a yellow oil, which was used without further purification.

Workup

  1. temperaturerefluxed 1 h
  2. temperatureAfter cooling to room temperature
  3. washwashed with water
  4. extractionThe organic extract
  5. dry with materialwas dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-6c7f277fb65044c1bbbd179f621aee60
Source dataset
uspto-grants-2013_09
Patent number
US08541380B2

Reaction notes

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