HCID 58786153, compound → HCID 58786197, compound

HRID 1375978Notes

Reaction equation

HRID 1375978 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:11][C@H:10]1[C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([CH2:46][OH:47])[CH:41]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[O:11][C@H:10]1[C:40]1[CH:41]=[C:42]([CH:43]=[CH:44][CH:45]=1)[CH:46]=[O:47])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 58786153HCID 58786153, compound

Product 1

HCID 58786197HCID 58786197, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

Manganese dioxide (20.4 g) was added to a solution of (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[3-(hydroxymethyl)phenyl]-D-glucitol (6.8 g) obtained in Reference Example 24 in chloroform (100 ml) and the mixture was refluxed with stirring for 1.5 hours. After separating the insoluble matter from the reaction mixture by filtration through celite at room temperature, the filtrate was concentrated. The residue was purified by silica gel column chromatography (n-hexane-ethyl acetate) to obtain 3-[(2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-yl]benzaldehyde (6.8 g).

Workup

  1. temperaturethe mixture was refluxed
  2. customAfter separating the insoluble matter from the reaction mixture
  3. filtrationby filtration through celite at room temperature
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by silica gel column chromatography (n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-b6f34da30c0649ee9633ddf568e34743
Source dataset
uspto-grants-2007_01
Patent number
US07169761B2

Reaction notes

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